Datasets:

juppy44
/

chembl-full

activity_comment string	activity_id int64	assay_chembl_id string	assay_description string	assay_type string	bao_format string	bao_label string	canonical_smiles string	data_validity_comment null	document_chembl_id string	document_journal string	document_year int64	molecule_chembl_id string	molecule_pref_name string	pchembl_value float64	qudt_units string	record_id int64	relation string	src_id int64	standard_flag int64	standard_relation string	standard_type string	standard_units string	standard_value float64	target_chembl_id string	target_organism string	target_pref_name string	target_tax_id string	text_value null	type string	units string	uo_units string	value string	ligand_efficiency__bei string	ligand_efficiency__le string	ligand_efficiency__lle string	ligand_efficiency__sei string	availability_type float64	chirality int64	first_approval float64	helm_notation string	inorganic_flag int64	max_phase string	molecule_type string	natural_product int64	oral bool	parenteral bool	pref_name string	prodrug int64	structure_type string	therapeutic_flag bool	topical bool	usan_stem string	usan_year float64	withdrawn_flag bool	molecule_structures__canonical_smiles string	molecule_structures__molfile string	molecule_structures__standard_inchi string	molecule_structures__standard_inchi_key string	molecule_properties__alogp float64	molecule_properties__aromatic_rings float64	molecule_properties__full_molformula string	molecule_properties__full_mwt string	molecule_properties__hba float64	molecule_properties__hbd float64	molecule_properties__heavy_atoms float64	molecule_properties__mw_freebase float64	molecule_properties__np_likeness_score string	molecule_properties__num_ro5_violations float64	molecule_properties__psa float64	molecule_properties__qed_weighted float64	molecule_properties__ro3_pass string	molecule_properties__rtb float64	molecule_hierarchy__active_chembl_id string	molecule_hierarchy__molecule_chembl_id string	molecule_hierarchy__parent_chembl_id string	molecule_synonyms_flat string	cross_references_flat string	assay_category null	assay_cell_type string	assay_organism string	assay_strain string	assay_subcellular_fraction string	assay_tax_id float64	assay_tissue string	assay_type_assay string	assay_type_description string	bao_format_assay string	bao_label_assay string	cell_chembl_id string	confidence_description string	confidence_score int64	description string	document_chembl_id_assay string	relationship_description string	relationship_type string	src_assay_id null	src_id_assay int64	target_chembl_id_assay string	tissue_chembl_id string	variant_sequence null	assay_parameters_flat string	target_organism_enriched string	target_pref_name_enriched string	species_group_flag bool	target_type string	tax_id float64	uniprot_accession string	component_description string	component_type string	component_id float64	n_components float64	mechanism_of_action string	action_type string	direct_interaction float64	disease_efficacy float64	mechanism_comment string	selectivity_comment string	binding_site_comment string	mesh_headings string	efo_terms string	max_phase_for_ind string	n_indications float64	doc__abstract string	doc__authors string	doc__doi string	doc__doi_chembl null	doc__first_page string	doc__issue string	doc__journal string	doc__patent_id null	doc__pubmed_id float64	doc__src_id int64	doc__title string	doc__volume string	doc__year int64
null	40,611	CHEMBL750936	In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 10 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein	B	BAO_0000219	cell-based format	Nc1nc(OCc2ccccc2)c2nc[nH]c2n1	null	CHEMBL1136584	Bioorg Med Chem Lett	2,003	CHEMBL407874	6-O-BENZYLGUANINE	null	null	309,926	=	1	0	=	Activity	(fM of O6-MeG removed) (mg of protein)-1	50	CHEMBL2864	Homo sapiens	Methylated-DNA--protein-cysteine methyltransferase	9606	null	Activity	(fM of O6-MeG removed) (mg of protein)-1	null	50.0	null	null	null	null	null	2	null	null	0	3.0	Small molecule	1	false	false	6-O-BENZYLGUANINE	0	MOL	false	false	null	null	false	Nc1nc(OCc2ccccc2)c2nc[nH]c2n1	RDKit 2D 18 20 0 0 0 0 0 0 0 0999 V2000 0.6696 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -0.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 0.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 0.9993 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -0.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5440 0.7443 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5440 2.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7594 0.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0289 1.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7594 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 1 5 2 0 1 11 1 0 4 3 1 0 6 3 1 0 4 5 1 0 16 4 2 0 6 8 1 0 16 7 1 0 17 7 2 0 8 10 2 0 8 15 1 0 17 9 1 0 18 9 1 0 10 12 1 0 18 11 2 0 12 13 2 0 13 14 1 0 14 15 2 0 16 18 1 0 M END > <chembl_id> CHEMBL407874 > <chembl_pref_name> 6-O-BENZYLGUANINE	InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)	KRWMERLEINMZFT-UHFFFAOYSA-N	1.51	3	C12H11N5O	241.25	5	2	18	241.25	-0.67	0	89.71	0.73	N	3	CHEMBL407874	CHEMBL407874	CHEMBL407874	6-o-benzylguanine [OTHER] \| NSC-637037 [RESEARCH_CODE] \| O6-benzylguanine [OTHER] \| O(6)-benzylguanine [OTHER]	null	null	MCF7	null	null	null	null	null	B	Binding	BAO_0000219	cell-based format	CHEMBL3308403	Homologous single protein target assigned	8	In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 10 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein	CHEMBL1136584	Homologous protein target assigned	H	null	1	CHEMBL2864	null	null	null	Homo sapiens	Methylated-DNA--protein-cysteine methyltransferase	false	SINGLE PROTEIN	9,606	P16455	Methylated-DNA--protein-cysteine methyltransferase	PROTEIN	1,194	1	null	null	null	null	null	null	null	Melanoma \| Glioblastoma \| Lymphoma \| Neoplasms \| Sarcoma \| Multiple Myeloma \| Lymphoma, T-Cell, Cutaneous \| Sezary Syndrome \| Mycosis Fungoides \| Gliosarcoma \| Central Nervous System Neoplasms \| Colorectal Neoplasms	cutaneous melanoma \| glioblastoma multiforme \| lymphoma \| neoplasm \| sarcoma \| multiple myeloma \| Cutaneous T-cell lymphoma \| Sezary's disease \| mycosis fungoides \| gliosarcoma \| Central Nervous System Neoplasm \| colorectal cancer	3.0	12	Novel radiolabeled O(6)-benzylguanine derivatives, 6-O-[(11)C]-[(methoxymethyl)benzyl]guanines ([(11)C]p-O(6)-MMBG, 1a; [(11)C]m-O(6)-MMBG, 1b; ([(11)C]o-O(6)-MMBG, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents for DNA repair protein, O(6)-alkylguanine-DNA alkyltransferase (AGT).	Liu X, Zheng QH, Fei X, Wang JQ, Ohannesian DW, Erickson LC, Stone KL, Hutchins GD.	10.1016/s0960-894x(02)01048-x	null	641	4	Bioorg Med Chem Lett	null	12,639,548	1	Synthesis and preliminary biological evaluation of 6-O-[11C]-[(methoxymethyl)benzyl]guanines, new potential PET breast cancer imaging agents for the DNA repair protein AGT.	13	2,003
null	40,612	CHEMBL713457	In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 50 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein	B	BAO_0000219	cell-based format	Nc1nc(OCc2ccccc2)c2nc[nH]c2n1	null	CHEMBL1136584	Bioorg Med Chem Lett	2,003	CHEMBL407874	6-O-BENZYLGUANINE	null	null	309,926	=	1	0	=	Activity	(fM of O6-MeG removed) (mg of protein)-1	19	CHEMBL2864	Homo sapiens	Methylated-DNA--protein-cysteine methyltransferase	9606	null	Activity	(fM of O6-MeG removed) (mg of protein)-1	null	19.0	null	null	null	null	null	2	null	null	0	3.0	Small molecule	1	false	false	6-O-BENZYLGUANINE	0	MOL	false	false	null	null	false	Nc1nc(OCc2ccccc2)c2nc[nH]c2n1	RDKit 2D 18 20 0 0 0 0 0 0 0 0999 V2000 0.6696 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -0.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 0.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 0.9993 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -0.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5440 0.7443 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5440 2.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6696 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7594 0.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0289 1.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7594 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 1 5 2 0 1 11 1 0 4 3 1 0 6 3 1 0 4 5 1 0 16 4 2 0 6 8 1 0 16 7 1 0 17 7 2 0 8 10 2 0 8 15 1 0 17 9 1 0 18 9 1 0 10 12 1 0 18 11 2 0 12 13 2 0 13 14 1 0 14 15 2 0 16 18 1 0 M END > <chembl_id> CHEMBL407874 > <chembl_pref_name> 6-O-BENZYLGUANINE	InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)	KRWMERLEINMZFT-UHFFFAOYSA-N	1.51	3	C12H11N5O	241.25	5	2	18	241.25	-0.67	0	89.71	0.73	N	3	CHEMBL407874	CHEMBL407874	CHEMBL407874	6-o-benzylguanine [OTHER] \| NSC-637037 [RESEARCH_CODE] \| O6-benzylguanine [OTHER] \| O(6)-benzylguanine [OTHER]	null	null	MCF7	null	null	null	null	null	B	Binding	BAO_0000219	cell-based format	CHEMBL3308403	Homologous single protein target assigned	8	In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 50 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein	CHEMBL1136584	Homologous protein target assigned	H	null	1	CHEMBL2864	null	null	null	Homo sapiens	Methylated-DNA--protein-cysteine methyltransferase	false	SINGLE PROTEIN	9,606	P16455	Methylated-DNA--protein-cysteine methyltransferase	PROTEIN	1,194	1	null	null	null	null	null	null	null	Melanoma \| Glioblastoma \| Lymphoma \| Neoplasms \| Sarcoma \| Multiple Myeloma \| Lymphoma, T-Cell, Cutaneous \| Sezary Syndrome \| Mycosis Fungoides \| Gliosarcoma \| Central Nervous System Neoplasms \| Colorectal Neoplasms	cutaneous melanoma \| glioblastoma multiforme \| lymphoma \| neoplasm \| sarcoma \| multiple myeloma \| Cutaneous T-cell lymphoma \| Sezary's disease \| mycosis fungoides \| gliosarcoma \| Central Nervous System Neoplasm \| colorectal cancer	3.0	12	Novel radiolabeled O(6)-benzylguanine derivatives, 6-O-[(11)C]-[(methoxymethyl)benzyl]guanines ([(11)C]p-O(6)-MMBG, 1a; [(11)C]m-O(6)-MMBG, 1b; ([(11)C]o-O(6)-MMBG, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents for DNA repair protein, O(6)-alkylguanine-DNA alkyltransferase (AGT).	Liu X, Zheng QH, Fei X, Wang JQ, Ohannesian DW, Erickson LC, Stone KL, Hutchins GD.	10.1016/s0960-894x(02)01048-x	null	641	4	Bioorg Med Chem Lett	null	12,639,548	1	Synthesis and preliminary biological evaluation of 6-O-[11C]-[(methoxymethyl)benzyl]guanines, new potential PET breast cancer imaging agents for the DNA repair protein AGT.	13	2,003
null	40,613	CHEMBL857692	Inhibitory concentration against HCV NS3 protease was determined	B	BAO_0000357	single protein format	CC[C@H](NC(=O)[C@H](CC1CCCCC1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c1cnccn1)[C@@H](C)CC)C(=O)C(=O)N[C@H](C(=O)O)C(C)C	null	CHEMBL1136650	Bioorg Med Chem Lett	2,003	CHEMBL13442	null	5.44	http://www.openphacts.org/units/Nanomolar	12,748	=	1	1	=	IC50	nM	3,600	CHEMBL4620	Hepatitis C virus genotype 1a (isolate 1) (HCV)	Genome polyprotein	11104	null	IC50	uM	UO_0000065	3.6	7.60	0.15	3.14	2.41	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CC[C@H](NC(=O)[C@H](CC1CCCCC1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c1cnccn1)[C@@H](C)CC)C(=O)C(=O)N[C@H](C(=O)O)C(C)C	RDKit 2D 51 52 0 0 1 0 0 0 0 0999 V2000 9.0417 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3250 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0375 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7542 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6042 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8917 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2583 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1792 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7542 -3.5792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4667 -3.5792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.8917 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3250 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9750 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4667 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1792 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6125 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1875 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 -3.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.3250 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0417 -4.4042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0375 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2583 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8917 -4.4042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1792 -4.4042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 -2.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1792 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 -4.8292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1792 -2.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3250 -4.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4750 -4.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9000 -3.5792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9750 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -1.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6125 -4.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4083 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3917 -1.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4083 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0417 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7542 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1875 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6125 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7000 -1.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8042 -0.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1875 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3250 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0417 -5.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8667 -0.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1042 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6917 -0.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 9 1 0 4 1 1 0 12 5 1 6 6 5 1 0 7 10 1 0 8 11 1 0 9 15 1 0 10 16 1 0 11 17 1 0 12 3 1 0 13 7 1 0 14 4 1 0 15 8 1 0 16 6 1 0 17 2 1 0 18 14 1 0 19 13 2 0 20 2 2 0 21 1 2 0 22 3 2 0 23 7 2 0 24 6 2 0 25 8 2 0 15 26 1 1 27 18 2 0 28 33 2 0 16 29 1 1 30 12 1 0 14 31 1 6 32 18 1 0 33 13 1 0 34 26 1 0 17 35 1 6 36 19 1 0 37 29 1 0 38 28 1 0 39 30 1 0 40 31 1 0 41 31 1 0 30 42 1 6 43 34 1 0 44 34 1 0 45 37 1 0 46 37 1 0 47 35 1 0 48 39 1 0 49 44 1 0 50 43 1 0 51 49 1 0 51 50 1 0 38 36 2 0 M END > <chembl_id> CHEMBL13442 > <chembl_pref_name> None	InChI=1S/C36H57N7O8/c1-8-22(7)29(43-32(46)25(17-20(3)4)40-33(47)27-19-37-15-16-38-27)34(48)41-26(18-23-13-11-10-12-14-23)31(45)39-24(9-2)30(44)35(49)42-28(21(5)6)36(50)51/h15-16,19-26,28-29H,8-14,17-18H2,1-7H3,(H,39,45)(H,40,47)(H,41,48)(H,42,49)(H,43,46)(H,50,51)/t22-,24-,25-,26-,28-,29-/m0/s1	DIROIABUGPDKJH-HPWCXNRPSA-N	2.3	1	C36H57N7O8	715.89	9	6	51	715.89	-0.19	2	225.65	0.11	N	20	CHEMBL13442	CHEMBL13442	CHEMBL13442	null	null	null	null	null	null	null	null	null	B	Binding	BAO_0000357	single protein format	null	Homologous single protein target assigned	8	Inhibitory concentration against HCV NS3 protease was determined	CHEMBL1136650	Homologous protein target assigned	H	null	1	CHEMBL4620	null	null	null	Hepatitis C virus genotype 1a (isolate 1) (HCV)	Genome polyprotein	false	SINGLE PROTEIN	11,104	P26664	Genome polyprotein	PROTEIN	5,042	1	null	null	null	null	null	null	null	null	null	null	null	Using a tetrapeptide-based alpha-ketoamide template, various amines and amino acids were incorporated to explore the prime side of the HCV NS3 protease catalytic site. Glycine carboxylic acid was found to be the most effective prime group. Further optimization yielded an inhibitor with IC(50) of 0.060 microM.	Han W, Hu Z, Jiang X, Wasserman ZR, Decicco CP.	10.1016/s0960-894x(03)00031-3	null	1111	6	Bioorg Med Chem Lett	null	12,643,923	1	Glycine alpha-ketoamides as HCV NS3 protease inhibitors.	13	2,003
null	40,615	CHEMBL615267	Inhibitory activity against inosine 5'-inosine monophosphate dehydrogenase type II (IMPDH II)	B	BAO_0000357	single protein format	Nc1ccc2cnccc2c1Br	null	CHEMBL1136691	Bioorg Med Chem Lett	2,003	CHEMBL27011	null	6.26	http://www.openphacts.org/units/Nanomolar	39,739	=	1	1	=	IC50	nM	550	CHEMBL2002	Homo sapiens	Inosine-5'-monophosphate dehydrogenase 2	9606	null	IC50	uM	UO_0000065	0.55	28.06	0.71	3.68	16.09	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	Nc1ccc2cnccc2c1Br	RDKit 2D 12 13 0 0 0 0 0 0 0 0999 V2000 0.4542 0.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2583 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1750 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6708 1.5208 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2500 1.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1750 1.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4625 1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4500 -0.5417 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.8875 0.2833 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9625 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9625 0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6708 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 1 2 0 4 12 1 0 5 2 2 0 6 3 1 0 7 6 2 0 8 1 1 0 9 3 1 0 10 5 1 0 11 2 1 0 12 11 2 0 5 7 1 0 10 4 2 0 M END > <chembl_id> CHEMBL27011 > <chembl_pref_name> None	InChI=1S/C9H7BrN2/c10-9-7-3-4-12-5-6(7)1-2-8(9)11/h1-5H,11H2	JDEBLBVBKMBILY-UHFFFAOYSA-N	2.58	2	C9H7BrN2	223.07	2	1	12	223.07	-0.61	0	38.91	0.7	Y	0	CHEMBL27011	CHEMBL27011	CHEMBL27011	null	null	null	null	null	null	null	null	null	B	Binding	BAO_0000357	single protein format	null	Homologous single protein target assigned	8	Inhibitory activity against inosine 5'-inosine monophosphate dehydrogenase type II (IMPDH II)	CHEMBL1136691	Homologous protein target assigned	H	null	1	CHEMBL2002	null	null	null	Homo sapiens	Inosine-5'-monophosphate dehydrogenase 2	false	SINGLE PROTEIN	9,606	P12268	Inosine-5'-monophosphate dehydrogenase 2	PROTEIN	333	1	null	null	null	null	null	null	null	null	null	null	null	Screening of our in-house compound collection led to the discovery of 5-bromo-6-amino-2-isoquinoline 1 as a weak inhibitor of IMPDH. Subsequent optimization of 1 afforded a series of novel 2-isoquinolinoaminooxazole-based inhibitors, represented by 17, with single-digit nanomolar potency against the enzyme.	Chen P, Norris D, Haslow KD, Murali Dhar TG, Pitts WJ, Watterson SH, Cheney DL, Bassolino DA, Fleener CA, Rouleau KA, Hollenbaugh DL, Townsend RM, Barrish JC, Iwanowicz EJ.	10.1016/s0960-894x(03)00107-0	null	1345	7	Bioorg Med Chem Lett	null	12,657,279	1	Identification of novel and potent isoquinoline aminooxazole-based IMPDH inhibitors.	13	2,003
null	40,616	CHEMBL761409	Ability to displace [3H]oxytocin from human OT receptor (hOT)	B	BAO_0000357	single protein format	Cc1cc2cc(C(=O)N3CCC(N4C(=O)OCc5ccccc54)CC3)ccc2[nH]1	null	CHEMBL1135944	Bioorg Med Chem Lett	2,002	CHEMBL32740	null	6.9	http://www.openphacts.org/units/Nanomolar	45,869	=	1	1	=	Ki	nM	125.89	CHEMBL2049	Homo sapiens	Oxytocin receptor	9606	null	Log Ki	null	UO_0000065	-6.9	17.72	0.32	2.66	10.51	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	Cc1cc2cc(C(=O)N3CCC(N4C(=O)OCc5ccccc54)CC3)ccc2[nH]1	RDKit 2D 29 33 0 0 0 0 0 0 0 0999 V2000 4.6792 -0.6667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4000 -0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6625 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6667 -3.1417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5792 -5.4750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9667 -0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7917 -4.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4000 0.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3750 -4.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0667 -4.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5875 -4.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7917 -5.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0792 -3.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6792 -1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9667 0.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9625 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3917 -1.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3875 -2.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9542 -2.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6792 0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1125 -0.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -4.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3667 -5.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0750 -5.6250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2542 -0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8917 -4.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2542 0.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 -0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 0.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 4 1 0 4 18 1 0 5 12 1 0 6 1 1 0 7 13 2 0 8 2 1 0 9 3 1 0 10 11 2 0 11 7 1 0 12 24 2 0 13 9 1 0 14 1 1 0 15 6 1 0 16 14 1 0 17 14 1 0 18 17 1 0 19 16 1 0 20 15 1 0 21 2 2 0 22 3 2 0 23 9 2 0 24 23 1 0 25 6 2 0 26 10 1 0 27 15 2 0 28 25 1 0 29 28 2 0 19 4 1 0 8 20 1 0 27 29 1 0 7 12 1 0 5 10 1 0 M END > <chembl_id> CHEMBL32740 > <chembl_pref_name> None	InChI=1S/C23H23N3O3/c1-15-12-18-13-16(6-7-20(18)24-15)22(27)25-10-8-19(9-11-25)26-21-5-3-2-4-17(21)14-29-23(26)28/h2-7,12-13,19,24H,8-11,14H2,1H3	CBFKPANXJWRIIF-UHFFFAOYSA-N	4.24	3	C23H23N3O3	389.45	3	1	29	389.45	-0.97	0	65.64	0.71	N	2	CHEMBL32740	CHEMBL32740	CHEMBL32740	null	null	null	null	null	null	null	null	null	B	Binding	BAO_0000357	single protein format	null	Homologous single protein target assigned	8	Ability to displace [3H]oxytocin from human OT receptor (hOT)	CHEMBL1135944	Homologous protein target assigned	H	null	1	CHEMBL2049	null	null	null	Homo sapiens	Oxytocin receptor	false	SINGLE PROTEIN	9,606	P30559	Oxytocin receptor	PROTEIN	389	1	null	null	null	null	null	null	null	null	null	null	null	Studies to discover novel, potent and selective oxytocin antagonists are reported. Combinatorial libraries designed to find novel replacements of fragments of oxytocin antagonist L-371,257, identified pyrimidine, thiazole, indole and benzofuran as potential alternatives to the benzoic acid moiety of L-371,257. Additional investigations identified indole and benzofuran derivatives with potent oxytocin antagonist activity.	Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, Scicinski J, Woollard PM.	10.1016/s0960-894x(02)00159-2	null	1399	10	Bioorg Med Chem Lett	null	11,992,786	1	Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives.	12	2,002
null	40,617	CHEMBL808229	Minimum fungicidal concentration against Saccharomyces cerevisiae(no antifungal activity)	F	BAO_0000218	organism-based format	CCCCCCCCOC(=O)c1cccc(O)c1	null	CHEMBL1134164	Bioorg Med Chem Lett	2,001	CHEMBL117843	null	null	http://www.openphacts.org/units/MicrogramPerMilliliter	222,259	=	1	0	=	MIC	ug.mL-1	null	CHEMBL361	Saccharomyces cerevisiae	Saccharomyces cerevisiae	4932	null	MIC	ug ml-1	UO_0000274	null	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCCCCCOC(=O)c1cccc(O)c1	RDKit 2D 18 18 0 0 0 0 0 0 0 0999 V2000 2.9375 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4042 -2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8792 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9417 -2.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3667 -2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 -2.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8375 -2.6625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4042 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8792 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3667 -3.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 -3.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9667 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0042 -6.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0042 -5.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4875 -5.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9667 -4.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4875 -4.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5167 -6.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 2 0 4 1 2 0 5 3 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 8 2 0 10 9 1 0 11 6 1 0 12 11 1 0 13 14 1 0 14 15 1 0 15 17 1 0 16 12 1 0 17 16 1 0 18 13 1 0 10 5 2 0 M END > <chembl_id> CHEMBL117843 > <chembl_pref_name> None	InChI=1S/C15H22O3/c1-2-3-4-5-6-7-11-18-15(17)13-9-8-10-14(16)12-13/h8-10,12,16H,2-7,11H2,1H3	LAJACIZEQBXWOS-UHFFFAOYSA-N	3.91	1	C15H22O3	250.34	3	1	18	250.34	0.16	0	46.53	0.56	N	8	CHEMBL117843	CHEMBL117843	CHEMBL117843	null	null	null	null	Saccharomyces cerevisiae	null	null	4,932	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Minimum fungicidal concentration against Saccharomyces cerevisiae(no antifungal activity)	CHEMBL1134164	Non-molecular target assigned	N	null	1	CHEMBL361	null	null	null	Saccharomyces cerevisiae	Saccharomyces cerevisiae	false	ORGANISM	4,932	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity.	Kubo I, Xiao P, Fujita K.	10.1016/s0960-894x(00)00656-9	null	347	3	Bioorg Med Chem Lett	null	11,212,107	1	Antifungal activity of octyl gallate: structural criteria and mode of action.	11	2,001
null	40,618	CHEMBL763559	Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP)	F	BAO_0000218	organism-based format	CCCCNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1	null	CHEMBL1133917	Bioorg Med Chem Lett	2,001	CHEMBL71066	null	7.7	http://www.openphacts.org/units/Nanomolar	123,884	=	1	1	=	IC50	nM	20	CHEMBL372	Homo sapiens	Homo sapiens	9606	null	IC50	uM	UO_0000065	0.02	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1	RDKit 2D 27 28 0 0 0 0 0 0 0 0999 V2000 3.0542 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5792 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8417 -3.8125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7250 -3.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5250 -2.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0667 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2750 -2.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 -2.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1167 -2.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1000 -3.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1333 -2.6500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3667 -2.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3542 -3.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7917 -2.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3375 -4.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3417 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5042 -4.0875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5167 -2.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9417 -2.3667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1458 -4.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6917 -2.7125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2000 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7208 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1250 -1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7083 -0.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1208 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 3 1 1 0 4 11 1 0 5 8 1 0 6 2 1 0 7 5 1 0 8 3 1 0 9 13 1 0 10 2 1 0 11 19 1 0 12 4 1 0 13 22 1 0 14 7 2 0 15 9 2 0 16 10 2 0 17 10 1 0 18 16 1 0 19 17 2 0 20 7 1 0 21 4 2 0 22 20 1 0 23 9 1 0 24 12 1 0 25 24 1 0 26 25 1 0 27 26 1 0 8 6 1 0 11 18 2 0 M END > <chembl_id> CHEMBL71066 > <chembl_pref_name> None	InChI=1S/C19H26N4O4/c1-2-3-9-22-19(20)14-6-4-13(5-7-14)16-11-15(27-23-16)12-17(24)21-10-8-18(25)26/h4-7,15H,2-3,8-12H2,1H3,(H2,20,22)(H,21,24)(H,25,26)	WFZZJCOUKAUMBN-UHFFFAOYSA-N	1.88	1	C19H26N4O4	374.44	5	4	27	374.44	-0.61	0	123.87	0.28	N	10	CHEMBL71066	CHEMBL71066	CHEMBL71066	null	null	null	null	Homo sapiens	null	null	9,606	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP)	CHEMBL1133917	Non-molecular target assigned	N	null	1	CHEMBL372	CHEMBL3559721	null	null	Homo sapiens	Homo sapiens	false	ORGANISM	9,606	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	Selective antagonism of the platelet GPIIb/IIIa receptor represents an attractive mechanism for the prevention and treatment of a number of thrombotic disease states. The antiplatelet activity of the oral GPIIb/IIIa receptor antagonists DMP 754 and DMP 802 have been disclosed. In this paper, the synthesis and biological evaluation of a series of potent N-substituted benzamidine isoxazolines are explored. The effect of benzamidine substitution on the duration of antiplatelet efficacy in dog is presented.	Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE.	10.1016/s0960-894x(01)00406-1	null	2201	16	Bioorg Med Chem Lett	null	11,514,170	1	Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists.	11	2,001
null	40,619	CHEMBL763559	Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP)	F	BAO_0000218	organism-based format	COc1ccccc1CNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1	null	CHEMBL1133917	Bioorg Med Chem Lett	2,001	CHEMBL71111	null	7.5	http://www.openphacts.org/units/Nanomolar	123,888	=	1	1	=	IC50	nM	32	CHEMBL372	Homo sapiens	Homo sapiens	9606	null	IC50	uM	UO_0000065	0.032	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	COc1ccccc1CNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1	RDKit 2D 32 34 0 0 0 0 0 0 0 0999 V2000 3.0542 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5792 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1333 -2.6500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7250 -3.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8417 -3.8125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5250 -2.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0667 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2750 -2.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 -2.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1167 -2.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1250 -1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1000 -3.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7208 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3667 -2.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7083 -0.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3542 -3.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7917 -2.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3417 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3375 -4.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5167 -2.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5042 -4.0875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9417 -2.3667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1458 -4.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6917 -2.7125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2000 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1125 -0.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9458 -1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1125 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5292 0.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3583 -0.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9458 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 3 4 1 0 4 13 1 0 5 1 1 0 6 9 1 0 7 2 1 0 8 6 1 0 9 5 1 0 10 15 1 0 11 14 1 0 12 2 1 0 13 22 1 0 14 3 1 0 15 25 1 0 16 11 2 0 17 8 2 0 18 10 2 0 19 12 2 0 20 12 1 0 21 19 1 0 22 20 2 0 23 8 1 0 24 4 2 0 25 23 1 0 26 10 1 0 27 16 1 0 28 11 1 0 29 16 1 0 30 27 1 0 31 28 2 0 32 31 1 0 9 7 1 0 21 13 2 0 29 32 2 0 M END > <chembl_id> CHEMBL71111 > <chembl_pref_name> None	InChI=1S/C23H26N4O5/c1-31-20-5-3-2-4-17(20)14-26-23(24)16-8-6-15(7-9-16)19-12-18(32-27-19)13-21(28)25-11-10-22(29)30/h2-9,18H,10-14H2,1H3,(H2,24,26)(H,25,28)(H,29,30)	HTKQOPDYLSNJQL-UHFFFAOYSA-N	2.28	2	C23H26N4O5	438.48	6	4	32	438.48	-0.74	0	133.1	0.33	N	10	CHEMBL71111	CHEMBL71111	CHEMBL71111	null	null	null	null	Homo sapiens	null	null	9,606	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP)	CHEMBL1133917	Non-molecular target assigned	N	null	1	CHEMBL372	CHEMBL3559721	null	null	Homo sapiens	Homo sapiens	false	ORGANISM	9,606	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	Selective antagonism of the platelet GPIIb/IIIa receptor represents an attractive mechanism for the prevention and treatment of a number of thrombotic disease states. The antiplatelet activity of the oral GPIIb/IIIa receptor antagonists DMP 754 and DMP 802 have been disclosed. In this paper, the synthesis and biological evaluation of a series of potent N-substituted benzamidine isoxazolines are explored. The effect of benzamidine substitution on the duration of antiplatelet efficacy in dog is presented.	Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE.	10.1016/s0960-894x(01)00406-1	null	2201	16	Bioorg Med Chem Lett	null	11,514,170	1	Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists.	11	2,001
null	40,620	CHEMBL812612	Inhibitory concentration against potent thrombin receptor-1 (PAR-1) on human platelets	B	BAO_0000019	assay format	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	null	CHEMBL1133830	Bioorg Med Chem Lett	2,001	CHEMBL97952	null	6.45	http://www.openphacts.org/units/Nanomolar	179,190	=	1	1	=	IC50	nM	359	CHEMBL3974	Homo sapiens	Proteinase-activated receptor 1	9606	null	IC50	nM	UO_0000065	359.0	14.80	0.28	0.53	9.08	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	RDKit 2D 32 34 0 0 0 0 0 0 0 0999 V2000 2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0292 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7917 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0875 -1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 1 1 0 5 4 1 0 6 11 1 0 7 12 2 0 8 7 1 0 9 1 1 0 10 13 1 0 11 10 2 0 12 10 1 0 13 9 1 0 14 2 2 0 15 7 1 0 16 6 1 0 17 13 2 0 18 8 1 0 19 3 1 0 20 4 2 0 21 5 2 0 22 15 1 0 23 15 1 0 24 16 1 0 25 16 1 0 26 16 1 0 27 15 1 0 28 19 1 0 29 28 1 0 30 31 2 0 31 20 1 0 32 29 1 0 3 5 1 0 21 30 1 0 8 6 2 0 M END > <chembl_id> CHEMBL97952 > <chembl_pref_name> None	InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3	WWLIKMQMTCGMJV-UHFFFAOYSA-N	5.91	3	C27H37N3O2	435.61	5	2	32	435.61	-0.54	1	71.01	0.47	N	6	CHEMBL97952	CHEMBL97952	CHEMBL97952	null	null	null	null	Homo sapiens	null	null	9,606	null	B	Binding	BAO_0000019	assay format	null	Direct single protein target assigned	9	Inhibitory concentration against potent thrombin receptor-1 (PAR-1) on human platelets	CHEMBL1133830	Direct protein target assigned	D	null	1	CHEMBL3974	null	null	null	Homo sapiens	Proteinase-activated receptor 1	false	SINGLE PROTEIN	9,606	P25116	Proteinase-activated receptor 1	PROTEIN	2,293	1	null	null	null	null	null	null	null	null	null	null	null	Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM.	Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G.	10.1016/s0960-894x(01)00555-8	null	2851	21	Bioorg Med Chem Lett	null	11,597,414	1	Potent, low molecular weight thrombin receptor antagonists.	11	2,001
null	40,621	CHEMBL699495	Inhibition of human platelet aggregation induced by high affinity thrombin receptor agonist peptide( ha-TRAP)	F	BAO_0000218	organism-based format	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	null	CHEMBL1133830	Bioorg Med Chem Lett	2,001	CHEMBL97952	null	6.08	http://www.openphacts.org/units/Nanomolar	179,190	=	1	1	=	IC50	nM	825	CHEMBL372	Homo sapiens	Homo sapiens	9606	null	IC50	nM	UO_0000065	825.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	RDKit 2D 32 34 0 0 0 0 0 0 0 0999 V2000 2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0292 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7917 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0875 -1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 1 1 0 5 4 1 0 6 11 1 0 7 12 2 0 8 7 1 0 9 1 1 0 10 13 1 0 11 10 2 0 12 10 1 0 13 9 1 0 14 2 2 0 15 7 1 0 16 6 1 0 17 13 2 0 18 8 1 0 19 3 1 0 20 4 2 0 21 5 2 0 22 15 1 0 23 15 1 0 24 16 1 0 25 16 1 0 26 16 1 0 27 15 1 0 28 19 1 0 29 28 1 0 30 31 2 0 31 20 1 0 32 29 1 0 3 5 1 0 21 30 1 0 8 6 2 0 M END > <chembl_id> CHEMBL97952 > <chembl_pref_name> None	InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3	WWLIKMQMTCGMJV-UHFFFAOYSA-N	5.91	3	C27H37N3O2	435.61	5	2	32	435.61	-0.54	1	71.01	0.47	N	6	CHEMBL97952	CHEMBL97952	CHEMBL97952	null	null	null	null	Homo sapiens	null	null	9,606	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Inhibition of human platelet aggregation induced by high affinity thrombin receptor agonist peptide( ha-TRAP)	CHEMBL1133830	Non-molecular target assigned	N	null	1	CHEMBL372	null	null	null	Homo sapiens	Homo sapiens	false	ORGANISM	9,606	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM.	Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G.	10.1016/s0960-894x(01)00555-8	null	2851	21	Bioorg Med Chem Lett	null	11,597,414	1	Potent, low molecular weight thrombin receptor antagonists.	11	2,001
null	40,622	CHEMBL699496	Inhibition of human platelet aggregation induced by thrombin	F	BAO_0000218	organism-based format	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	null	CHEMBL1133830	Bioorg Med Chem Lett	2,001	CHEMBL97952	null	5	http://www.openphacts.org/units/Nanomolar	179,190	=	1	1	=	IC50	nM	10,000	CHEMBL372	Homo sapiens	Homo sapiens	9606	null	IC50	nM	UO_0000065	10000.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21	RDKit 2D 32 34 0 0 0 0 0 0 0 0999 V2000 2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0292 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7917 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0875 -1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 1 1 0 5 4 1 0 6 11 1 0 7 12 2 0 8 7 1 0 9 1 1 0 10 13 1 0 11 10 2 0 12 10 1 0 13 9 1 0 14 2 2 0 15 7 1 0 16 6 1 0 17 13 2 0 18 8 1 0 19 3 1 0 20 4 2 0 21 5 2 0 22 15 1 0 23 15 1 0 24 16 1 0 25 16 1 0 26 16 1 0 27 15 1 0 28 19 1 0 29 28 1 0 30 31 2 0 31 20 1 0 32 29 1 0 3 5 1 0 21 30 1 0 8 6 2 0 M END > <chembl_id> CHEMBL97952 > <chembl_pref_name> None	InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3	WWLIKMQMTCGMJV-UHFFFAOYSA-N	5.91	3	C27H37N3O2	435.61	5	2	32	435.61	-0.54	1	71.01	0.47	N	6	CHEMBL97952	CHEMBL97952	CHEMBL97952	null	null	null	null	Homo sapiens	null	null	9,606	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Inhibition of human platelet aggregation induced by thrombin	CHEMBL1133830	Non-molecular target assigned	N	null	1	CHEMBL372	null	null	null	Homo sapiens	Homo sapiens	false	ORGANISM	9,606	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM.	Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G.	10.1016/s0960-894x(01)00555-8	null	2851	21	Bioorg Med Chem Lett	null	11,597,414	1	Potent, low molecular weight thrombin receptor antagonists.	11	2,001
null	40,624	CHEMBL737009	Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL90025	null	null	null	164,080	=	1	0	=	Cholesterol	mM l-1	2.3	CHEMBL375	Mus musculus	Mus musculus	10090	null	Cholesterol	mM l-1	null	2.3	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	RDKit 2D 19 20 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 3 1 0 5 1 1 0 6 1 2 0 7 4 2 0 8 5 1 0 9 4 1 0 10 14 2 0 11 10 1 0 12 8 1 0 13 8 2 0 14 13 1 0 15 12 2 0 16 2 2 0 17 3 2 0 18 19 2 0 19 16 1 0 10 15 1 0 18 17 1 0 M END > <chembl_id> CHEMBL90025 > <chembl_pref_name> None	InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19)	WJSPLHRLEZJTRR-UHFFFAOYSA-N	3.29	2	C14H10ClNO3	275.69	2	2	19	275.69	-1.26	0	66.4	0.9	N	3	CHEMBL90025	CHEMBL90025	CHEMBL90025	null	null	null	null	Mus musculus	null	null	10,090	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	CHEMBL3559721	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,626	CHEMBL745439	Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL90025	null	null	null	164,080	=	1	0	=	Triglycerides	mM l-1	0.86	CHEMBL375	Mus musculus	Mus musculus	10090	null	Triglycerides	mM l-1	null	0.8600000000000001	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	RDKit 2D 19 20 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 3 1 0 5 1 1 0 6 1 2 0 7 4 2 0 8 5 1 0 9 4 1 0 10 14 2 0 11 10 1 0 12 8 1 0 13 8 2 0 14 13 1 0 15 12 2 0 16 2 2 0 17 3 2 0 18 19 2 0 19 16 1 0 10 15 1 0 18 17 1 0 M END > <chembl_id> CHEMBL90025 > <chembl_pref_name> None	InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19)	WJSPLHRLEZJTRR-UHFFFAOYSA-N	3.29	2	C14H10ClNO3	275.69	2	2	19	275.69	-1.26	0	66.4	0.9	N	3	CHEMBL90025	CHEMBL90025	CHEMBL90025	null	null	null	null	Mus musculus	null	null	10,090	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	CHEMBL3559721	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,628	CHEMBL733793	Animal body weight was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL90025	null	null	http://qudt.org/vocab/unit#Gram	164,080	=	1	0	=	Body weight	g	25	CHEMBL375	Mus musculus	Mus musculus	10090	null	Body weight	g	UO_0000021	25.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	RDKit 2D 19 20 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 3 1 0 5 1 1 0 6 1 2 0 7 4 2 0 8 5 1 0 9 4 1 0 10 14 2 0 11 10 1 0 12 8 1 0 13 8 2 0 14 13 1 0 15 12 2 0 16 2 2 0 17 3 2 0 18 19 2 0 19 16 1 0 10 15 1 0 18 17 1 0 M END > <chembl_id> CHEMBL90025 > <chembl_pref_name> None	InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19)	WJSPLHRLEZJTRR-UHFFFAOYSA-N	3.29	2	C14H10ClNO3	275.69	2	2	19	275.69	-1.26	0	66.4	0.9	N	3	CHEMBL90025	CHEMBL90025	CHEMBL90025	null	null	null	null	Mus musculus	null	null	10,090	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Animal body weight was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	null	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,629	CHEMBL733794	Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL90025	null	null	http://qudt.org/vocab/unit#Gram	164,080	=	1	0	=	Body weight	g	28	CHEMBL375	Mus musculus	Mus musculus	10090	null	Body weight	g	UO_0000021	28.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1	RDKit 2D 19 20 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 3 2 1 0 4 3 1 0 5 1 1 0 6 1 2 0 7 4 2 0 8 5 1 0 9 4 1 0 10 14 2 0 11 10 1 0 12 8 1 0 13 8 2 0 14 13 1 0 15 12 2 0 16 2 2 0 17 3 2 0 18 19 2 0 19 16 1 0 10 15 1 0 18 17 1 0 M END > <chembl_id> CHEMBL90025 > <chembl_pref_name> None	InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19)	WJSPLHRLEZJTRR-UHFFFAOYSA-N	3.29	2	C14H10ClNO3	275.69	2	2	19	275.69	-1.26	0	66.4	0.9	N	3	CHEMBL90025	CHEMBL90025	CHEMBL90025	null	null	null	null	Mus musculus	null	null	10,090	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	null	null	ROUTE=None None	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,630	CHEMBL737009	Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nn1cnnc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL262903	null	null	null	164,077	=	1	0	=	Cholesterol	mM l-1	2.46	CHEMBL375	Mus musculus	Mus musculus	10090	null	Cholesterol	mM l-1	null	2.46	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nn1cnnc1	RDKit 2D 17 18 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 3 8 2 0 4 9 2 0 5 1 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 2 1 0 10 7 1 0 11 1 2 0 12 10 2 0 13 10 1 0 14 5 2 0 15 7 2 0 16 17 2 0 17 14 1 0 4 3 1 0 15 16 1 0 M END > <chembl_id> CHEMBL262903 > <chembl_pref_name> None	InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17)	JXXNYVAHSXIBNI-UHFFFAOYSA-N	0.36	2	C10H8N4O3	232.20	5	2	17	232.2	-1.14	0	97.11	0.8	N	3	CHEMBL262903	CHEMBL262903	CHEMBL262903	null	null	null	null	Mus musculus	null	null	10,090	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	CHEMBL3559721	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,631	CHEMBL737010	Plasma cholesterol level was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nn1cnnc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL262903	null	null	null	164,077	=	1	0	=	Cholesterol	mM l-1	2.95	CHEMBL375	Mus musculus	Mus musculus	10090	null	Cholesterol	mM l-1	null	2.95	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nn1cnnc1	RDKit 2D 17 18 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 3 8 2 0 4 9 2 0 5 1 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 2 1 0 10 7 1 0 11 1 2 0 12 10 2 0 13 10 1 0 14 5 2 0 15 7 2 0 16 17 2 0 17 14 1 0 4 3 1 0 15 16 1 0 M END > <chembl_id> CHEMBL262903 > <chembl_pref_name> None	InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17)	JXXNYVAHSXIBNI-UHFFFAOYSA-N	0.36	2	C10H8N4O3	232.20	5	2	17	232.2	-1.14	0	97.11	0.8	N	3	CHEMBL262903	CHEMBL262903	CHEMBL262903	null	null	null	null	Mus musculus	null	null	10,090	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Plasma cholesterol level was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	CHEMBL3559721	null	ROUTE=None None	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,632	CHEMBL745439	Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nn1cnnc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL262903	null	null	null	164,077	=	1	0	=	Triglycerides	mM l-1	1.12	CHEMBL375	Mus musculus	Mus musculus	10090	null	Triglycerides	mM l-1	null	1.12	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nn1cnnc1	RDKit 2D 17 18 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 3 8 2 0 4 9 2 0 5 1 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 2 1 0 10 7 1 0 11 1 2 0 12 10 2 0 13 10 1 0 14 5 2 0 15 7 2 0 16 17 2 0 17 14 1 0 4 3 1 0 15 16 1 0 M END > <chembl_id> CHEMBL262903 > <chembl_pref_name> None	InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17)	JXXNYVAHSXIBNI-UHFFFAOYSA-N	0.36	2	C10H8N4O3	232.20	5	2	17	232.2	-1.14	0	97.11	0.8	N	3	CHEMBL262903	CHEMBL262903	CHEMBL262903	null	null	null	null	Mus musculus	null	null	10,090	Plasma	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	CHEMBL3559721	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,634	CHEMBL733793	Animal body weight was evaluated in Swiss white mice before treatment with the compound	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nn1cnnc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL262903	null	null	http://qudt.org/vocab/unit#Gram	164,077	=	1	0	=	Body weight	g	35	CHEMBL375	Mus musculus	Mus musculus	10090	null	Body weight	g	UO_0000021	35.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nn1cnnc1	RDKit 2D 17 18 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 3 8 2 0 4 9 2 0 5 1 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 2 1 0 10 7 1 0 11 1 2 0 12 10 2 0 13 10 1 0 14 5 2 0 15 7 2 0 16 17 2 0 17 14 1 0 4 3 1 0 15 16 1 0 M END > <chembl_id> CHEMBL262903 > <chembl_pref_name> None	InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17)	JXXNYVAHSXIBNI-UHFFFAOYSA-N	0.36	2	C10H8N4O3	232.20	5	2	17	232.2	-1.14	0	97.11	0.8	N	3	CHEMBL262903	CHEMBL262903	CHEMBL262903	null	null	null	null	Mus musculus	null	null	10,090	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Animal body weight was evaluated in Swiss white mice before treatment with the compound	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	null	null	null	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	40,635	CHEMBL733794	Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	F	BAO_0000218	organism-based format	O=C(O)c1ccccc1C(=O)Nn1cnnc1	null	CHEMBL1133800	Bioorg Med Chem Lett	2,001	CHEMBL262903	null	null	http://qudt.org/vocab/unit#Gram	164,077	=	1	0	=	Body weight	g	39	CHEMBL375	Mus musculus	Mus musculus	10090	null	Body weight	g	UO_0000021	39.0	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	O=C(O)c1ccccc1C(=O)Nn1cnnc1	RDKit 2D 17 18 0 0 0 0 0 0 0 0999 V2000 4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 3 8 2 0 4 9 2 0 5 1 1 0 6 1 1 0 7 5 1 0 8 2 1 0 9 2 1 0 10 7 1 0 11 1 2 0 12 10 2 0 13 10 1 0 14 5 2 0 15 7 2 0 16 17 2 0 17 14 1 0 4 3 1 0 15 16 1 0 M END > <chembl_id> CHEMBL262903 > <chembl_pref_name> None	InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17)	JXXNYVAHSXIBNI-UHFFFAOYSA-N	0.36	2	C10H8N4O3	232.20	5	2	17	232.2	-1.14	0	97.11	0.8	N	3	CHEMBL262903	CHEMBL262903	CHEMBL262903	null	null	null	null	Mus musculus	null	null	10,090	null	F	Functional	BAO_0000218	organism-based format	null	Target assigned is non-molecular	1	Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days	CHEMBL1133800	Non-molecular target assigned	N	null	1	CHEMBL375	null	null	ROUTE=None None	Mus musculus	Mus musculus	false	ORGANISM	10,090	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.	Sena VL, Srivastava RM, Oliveira SP, Lima VL.	10.1016/s0960-894x(01)00540-6	null	2671	20	Bioorg Med Chem Lett	null	11,591,498	1	Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity.	11	2,001
null	34,377	CHEMBL636019	True partition coefficient corrected for ionization was determined	P	BAO_0000100	small-molecule physicochemical format	CN(C)CCc1c[nH]c2cccc(O)c12	null	CHEMBL1121785	J Med Chem	1,981	CHEMBL65547	PSILOCIN	null	null	113,388	=	1	0	=	pKa	null	42.1	CHEMBL2362975	null	No relevant target	null	null	pKa	null	null	42.1	null	null	null	null	null	2	null	null	0	2.0	Small molecule	1	false	false	PSILOCIN	0	MOL	false	false	deu-	null	false	CN(C)CCc1c[nH]c2cccc(O)c12	RDKit 2D 15 16 0 0 0 0 0 0 0 0999 V2000 3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 8 4 2 0 5 6 1 0 7 8 1 0 9 5 1 0 4 1 1 0 7 10 1 0 8 9 1 0 10 11 1 0 11 12 1 0 2 3 1 0 12 13 1 0 6 7 2 0 12 14 1 0 3 9 2 0 4 15 1 0 M END > <chembl_id> CHEMBL65547 > <chembl_pref_name> PSILOCIN	InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3	SPCIYGNTAMCTRO-UHFFFAOYSA-N	1.98	2	C12H16N2O	204.27	2	2	15	204.27	0.31	0	39.26	0.8	Y	3	CHEMBL65547	CHEMBL65547	CHEMBL65547	4-ho-dmt [OTHER] \| Psilocin [OTHER] \| Psilocyn [OTHER]	null	null	null	null	null	null	null	null	P	Physicochemical	BAO_0000100	small-molecule physicochemical format	null	Default value - Target unknown or has yet to be assigned	0	True partition coefficient corrected for ionization was determined	CHEMBL1121785	Default value - Target has yet to be curated	U	null	1	CHEMBL2362975	null	null	null	null	No relevant target	false	NO TARGET	null	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively.	Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE.	10.1021/jm00134a016	null	206	2	J Med Chem	null	6,259,355	1	Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy.	24	1,981
null	34,378	CHEMBL638404	Partition coefficient of octanol and water was determined	P	BAO_0000100	small-molecule physicochemical format	CN(C)CCc1c[nH]c2cccc(O)c12	null	CHEMBL1121785	J Med Chem	1,981	CHEMBL65547	PSILOCIN	null	null	113,388	=	1	0	=	Poct	null	0.68	CHEMBL2362975	null	No relevant target	null	null	Poct	null	null	0.68	null	null	null	null	null	2	null	null	0	2.0	Small molecule	1	false	false	PSILOCIN	0	MOL	false	false	deu-	null	false	CN(C)CCc1c[nH]c2cccc(O)c12	RDKit 2D 15 16 0 0 0 0 0 0 0 0999 V2000 3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 8 4 2 0 5 6 1 0 7 8 1 0 9 5 1 0 4 1 1 0 7 10 1 0 8 9 1 0 10 11 1 0 11 12 1 0 2 3 1 0 12 13 1 0 6 7 2 0 12 14 1 0 3 9 2 0 4 15 1 0 M END > <chembl_id> CHEMBL65547 > <chembl_pref_name> PSILOCIN	InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3	SPCIYGNTAMCTRO-UHFFFAOYSA-N	1.98	2	C12H16N2O	204.27	2	2	15	204.27	0.31	0	39.26	0.8	Y	3	CHEMBL65547	CHEMBL65547	CHEMBL65547	4-ho-dmt [OTHER] \| Psilocin [OTHER] \| Psilocyn [OTHER]	null	null	null	null	null	null	null	null	P	Physicochemical	BAO_0000100	small-molecule physicochemical format	null	Default value - Target unknown or has yet to be assigned	0	Partition coefficient of octanol and water was determined	CHEMBL1121785	Default value - Target has yet to be curated	U	null	1	CHEMBL2362975	null	null	null	null	No relevant target	false	NO TARGET	null	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively.	Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE.	10.1021/jm00134a016	null	206	2	J Med Chem	null	6,259,355	1	Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy.	24	1,981
null	34,379	CHEMBL637888	Partition coefficient (logP)	P	BAO_0000100	small-molecule physicochemical format	CN(C)CCc1c[nH]c2cccc(O)c12	null	CHEMBL1121785	J Med Chem	1,981	CHEMBL65547	PSILOCIN	null	null	113,388	=	1	1	=	LogP	null	1.45	CHEMBL2362975	null	No relevant target	null	null	logP	null	null	1.45	null	null	null	null	null	2	null	null	0	2.0	Small molecule	1	false	false	PSILOCIN	0	MOL	false	false	deu-	null	false	CN(C)CCc1c[nH]c2cccc(O)c12	RDKit 2D 15 16 0 0 0 0 0 0 0 0999 V2000 3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 8 4 2 0 5 6 1 0 7 8 1 0 9 5 1 0 4 1 1 0 7 10 1 0 8 9 1 0 10 11 1 0 11 12 1 0 2 3 1 0 12 13 1 0 6 7 2 0 12 14 1 0 3 9 2 0 4 15 1 0 M END > <chembl_id> CHEMBL65547 > <chembl_pref_name> PSILOCIN	InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3	SPCIYGNTAMCTRO-UHFFFAOYSA-N	1.98	2	C12H16N2O	204.27	2	2	15	204.27	0.31	0	39.26	0.8	Y	3	CHEMBL65547	CHEMBL65547	CHEMBL65547	4-ho-dmt [OTHER] \| Psilocin [OTHER] \| Psilocyn [OTHER]	null	null	null	null	null	null	null	null	P	Physicochemical	BAO_0000100	small-molecule physicochemical format	null	Default value - Target unknown or has yet to be assigned	0	Partition coefficient (logP)	CHEMBL1121785	Default value - Target has yet to be curated	U	null	1	CHEMBL2362975	null	null	null	null	No relevant target	false	NO TARGET	null	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively.	Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE.	10.1021/jm00134a016	null	206	2	J Med Chem	null	6,259,355	1	Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy.	24	1,981
null	34,380	CHEMBL668662	Inhibition of dihydrofolate reductase from bovine liver	B	BAO_0000019	assay format	CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1	null	CHEMBL1121828	J Med Chem	1,981	CHEMBL31235	null	null	null	295,584	=	1	0	=	Log 1/Ki app	null	5.78	CHEMBL1075051	Bos taurus	Dihydrofolate reductase	9913	null	Log 1/Ki app	null	null	5.78	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1	RDKit 2D 24 25 0 0 0 0 0 0 0 0999 V2000 0.7417 -4.2792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2542 -3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7792 -4.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7417 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2542 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7792 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2917 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -4.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2500 -3.3792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2167 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -5.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -5.7750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8667 -4.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8667 -4.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -6.0667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8125 -6.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -8.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 -8.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7625 -7.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2917 -6.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -7.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2250 -9.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 3 2 1 0 4 1 1 0 5 4 2 0 6 5 1 0 7 3 1 0 8 7 1 0 9 2 1 0 10 4 1 0 11 8 2 0 12 11 1 0 13 12 1 0 14 15 2 0 15 8 1 0 16 14 1 0 17 13 1 0 18 17 1 0 19 20 1 0 20 21 1 0 21 23 1 0 22 18 1 0 23 22 1 0 24 19 1 0 6 3 2 0 16 12 2 0 M END > <chembl_id> CHEMBL31235 > <chembl_pref_name> None	InChI=1S/C19H28N4O/c1-2-3-4-5-6-7-11-24-17-10-8-9-15(13-17)12-16-14-22-19(21)23-18(16)20/h8-10,13-14H,2-7,11-12H2,1H3,(H4,20,21,22,23)	RNZGHILIUCETNY-UHFFFAOYSA-N	3.97	2	C19H28N4O	328.46	5	2	24	328.46	-0.34	0	87.05	0.64	N	10	CHEMBL31235	CHEMBL31235	CHEMBL31235	null	null	null	null	Bos taurus	null	null	9,913	null	B	Binding	BAO_0000019	assay format	null	Direct single protein target assigned	9	Inhibition of dihydrofolate reductase from bovine liver	CHEMBL1121828	Direct protein target assigned	D	null	1	CHEMBL1075051	null	null	null	Bos taurus	Dihydrofolate reductase	false	SINGLE PROTEIN	9,913	P00376	Dihydrofolate reductase	PROTEIN	4,114	1	null	null	null	null	null	null	null	null	null	null	null	In our previous publication (Blaney, J. M.; Dietrich, S. W.; Reynolds, M. A.; Hansch, C. J. Med. Chem. 1979, 22, 614), correlation equations were presented for the inhibition of bovine liver and Escherichia coli dihydrofolate reductase (DHFR) by 5-(substituted benzyl)-2,4-diaminopyrimidines. These equations brought out differences in the way these two enzymes interact with substituents, which explain the high selectivity of drugs like trimethoprim. We have tested and further developed these equations in this report. It is of particular interest that our previously published correlation equation for E. coli DHFR accurately predicted the potency of a commercial competitor of trimethoprim (tetroxoprim) now in clinical use. We believe that new and effective competitors for trimethoprim can be designed by means of the two correlation equations.	Li RL, Dietrich SW, Hansch C.	10.1021/jm00137a012	null	538	5	J Med Chem	null	7,017,146	1	Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines.	24	1,981
null	34,381	CHEMBL668773	Compound is evaluated for the inhibition of dihydrofolate reductase from Escherichia coli	B	BAO_0000357	single protein format	CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1	null	CHEMBL1121828	J Med Chem	1,981	CHEMBL31235	null	null	null	295,584	=	1	0	=	Log 1/Ki app	null	6.25	CHEMBL1809	Escherichia coli	Dihydrofolate reductase	562	null	Log 1/Ki app	null	null	6.25	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1	RDKit 2D 24 25 0 0 0 0 0 0 0 0999 V2000 0.7417 -4.2792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2542 -3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7792 -4.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7417 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2542 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7792 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2917 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -4.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2500 -3.3792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2167 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -5.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -5.7750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8667 -4.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8667 -4.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -6.0667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8125 -6.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -8.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 -8.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7625 -7.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2917 -6.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -7.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2250 -9.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 3 2 1 0 4 1 1 0 5 4 2 0 6 5 1 0 7 3 1 0 8 7 1 0 9 2 1 0 10 4 1 0 11 8 2 0 12 11 1 0 13 12 1 0 14 15 2 0 15 8 1 0 16 14 1 0 17 13 1 0 18 17 1 0 19 20 1 0 20 21 1 0 21 23 1 0 22 18 1 0 23 22 1 0 24 19 1 0 6 3 2 0 16 12 2 0 M END > <chembl_id> CHEMBL31235 > <chembl_pref_name> None	InChI=1S/C19H28N4O/c1-2-3-4-5-6-7-11-24-17-10-8-9-15(13-17)12-16-14-22-19(21)23-18(16)20/h8-10,13-14H,2-7,11-12H2,1H3,(H4,20,21,22,23)	RNZGHILIUCETNY-UHFFFAOYSA-N	3.97	2	C19H28N4O	328.46	5	2	24	328.46	-0.34	0	87.05	0.64	N	10	CHEMBL31235	CHEMBL31235	CHEMBL31235	null	null	null	null	Escherichia coli	null	null	562	null	B	Binding	BAO_0000357	single protein format	null	Direct single protein target assigned	9	Compound is evaluated for the inhibition of dihydrofolate reductase from Escherichia coli	CHEMBL1121828	Direct protein target assigned	D	null	1	CHEMBL1809	null	null	null	Escherichia coli	Dihydrofolate reductase	false	SINGLE PROTEIN	562	P0ABQ4	Dihydrofolate reductase	PROTEIN	103	1	null	null	null	null	null	null	null	null	null	null	null	In our previous publication (Blaney, J. M.; Dietrich, S. W.; Reynolds, M. A.; Hansch, C. J. Med. Chem. 1979, 22, 614), correlation equations were presented for the inhibition of bovine liver and Escherichia coli dihydrofolate reductase (DHFR) by 5-(substituted benzyl)-2,4-diaminopyrimidines. These equations brought out differences in the way these two enzymes interact with substituents, which explain the high selectivity of drugs like trimethoprim. We have tested and further developed these equations in this report. It is of particular interest that our previously published correlation equation for E. coli DHFR accurately predicted the potency of a commercial competitor of trimethoprim (tetroxoprim) now in clinical use. We believe that new and effective competitors for trimethoprim can be designed by means of the two correlation equations.	Li RL, Dietrich SW, Hansch C.	10.1021/jm00137a012	null	538	5	J Med Chem	null	7,017,146	1	Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines.	24	1,981
null	34,382	CHEMBL847678	Sweet potency as logarithm of sweet potency (log SP) relative to sucrose	F	BAO_0000019	assay format	C[C@@H](Cc1ccco1)NC(=O)[C@H](N)CC(=O)O	null	CHEMBL1121833	J Med Chem	1,981	CHEMBL154919	null	null	null	302,439	=	1	0	=	Log SP	null	1.16	CHEMBL612545	null	Unchecked	null	null	Log SP	null	null	1.16	null	null	null	null	-1	-1	null	null	-1	null	Small molecule	0	false	false	null	-1	MOL	false	false	null	null	false	C[C@@H](Cc1ccco1)NC(=O)[C@H](N)CC(=O)O	RDKit 2D 17 17 0 0 1 0 0 0 0 0999 V2000 -2.0250 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0625 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5083 -0.6875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5458 -0.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5833 -0.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0542 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1167 -1.5792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4708 -0.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 -1.5875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6000 -0.7375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 -1.7042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0042 -1.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5833 -0.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9833 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5458 -0.0875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1000 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9833 -1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 3 1 1 0 4 1 1 0 5 2 1 0 6 8 1 0 7 6 1 0 8 14 1 0 9 1 2 0 10 6 2 0 11 7 1 0 12 10 1 0 13 5 2 0 14 3 1 0 4 15 1 1 16 5 1 0 14 17 1 6 12 11 2 0 M END > <chembl_id> CHEMBL154919 > <chembl_pref_name> None	InChI=1S/C11H16N2O4/c1-7(5-8-3-2-4-17-8)13-11(16)9(12)6-10(14)15/h2-4,7,9H,5-6,12H2,1H3,(H,13,16)(H,14,15)/t7-,9+/m0/s1	VOQPIRFCQUFIFQ-IONNQARKSA-N	0.13	1	C11H16N2O4	240.26	4	3	17	240.26	-0.55	0	105.56	0.65	N	6	CHEMBL154919	CHEMBL154919	CHEMBL154919	null	null	null	null	null	null	null	null	null	F	Functional	BAO_0000019	assay format	null	Default value - Target unknown or has yet to be assigned	0	Sweet potency as logarithm of sweet potency (log SP) relative to sucrose	CHEMBL1121833	Default value - Target has yet to be curated	U	null	1	CHEMBL612545	null	null	null	null	Unchecked	false	UNCHECKED	null	null	null	null	null	0	null	null	null	null	null	null	null	null	null	null	null	The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures.	Iwamura H.	10.1021/jm00137a018	null	572	5	J Med Chem	null	7,241,515	1	Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology.	24	1,981

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ChEMBL Full Dataset

A flat, fully-joined export of the ChEMBL database (1,980 rows, 139 columns).

What's included

Each row is one bioactivity measurement (IC50, Ki, EC50, Kd, GI50 etc.) enriched with:

Source	Key columns
Activity	`pchembl_value`, `standard_type/value/units`, `activity_comment`, `ligand_efficiency`
Molecule	`canonical_smiles`, `standard_inchi`, all physicochemical properties, `max_phase`, `indication_class`, synonyms
Assay	`description` (free text), `confidence_score`, `assay_type`, cell/tissue/organism context
Target	`pref_name`, `target_type`, `uniprot_accession`, `component_description`
Mechanism	`mechanism_of_action`, `action_type`, `mechanism_comment`, `selectivity_comment`
Drug indications	`mesh_headings`, `efo_terms`, `max_phase_for_ind`
Document	`doc__title`, `doc__abstract`, `doc__doi`, `doc__pubmed_id`

Usage

from datasets import load_dataset
ds = load_dataset("juppy44/chembl-full")
df = ds['train'].to_pandas()

License

ChEMBL data is provided under CC BY-SA 3.0. Cite: Zdrazil et al., Nucleic Acids Research 2023. DOI: 10.1093/nar/gkad1004

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1.34 MB

Number of rows:

1,980