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from tests import TestHelper
class AmideCouplingTest(TestHelper.ReactionTestCase):
reactant_names = ["amine", "acid"]
def setUp(self):
self.set_reaction(ClickReaction.AmideCoupling)
def test_one_product(self):
reactants = [
# Ammonia and ammonium with acetic acid
(("N", "OC(C)=O"), "O=C(C)N"),
(("[NH4+]", "OC(C)=O"), "O=C(C)N"),
(("N(-[H])(-[H])(-[H])", "OC(C)=O"), "O=C(C)N"),
# Primary amines with simple acids
(("CN", "OC=O"), "CNC=O"),
(("CCN", "OC(C)=O"), "O=C(C)NCC"),
(("CN", "OC(C1=CC=CC=C1)=O"), "O=C(C1=CC=CC=C1)NC"),
(("NC1=CC=CC(CN)=C1", "OC(C)=O"), "NC1=CC=CC(CNC(C)=O)=C1"),
# Secondary amines with simple acids
(("CNC", "OC(C)=O"), "O=C(C)N(C)C"),
# Primary ammonium with simple acids
(("CC[NH3+]", "OC(C)=O"), "O=C(C)NCC"),
# Secondary ammonium with simple acids
(("C[NH2+]C", "OC(C)=O"), "O=C(C)N(C)C"),
# Simple amine with carboxylate
(("CCN", "[O-]C(C)=O"), "O=C(C)NCC"),
# Secondary ammonium with carboxylate
(("C[NH2+]C", "[O-]C(C(C1=CC=CC=C1)(F)Cl)=O"), "O=C(C(C1=CC=CC=C1)(F)Cl)N(C)C"),
#
# Amine with active esters
#
# N-Hydroxysuccinimide
(("CCN", "CCC(ON1C(CCC1=O)=O)=O"), "CCC(NCC)=O"),
# N-Sulfo-Hydroxysuccinimide
(("CCN", "CCC(ON1C(CC(S(=O)(O)=O)C1=O)=O)=O"), "CCC(NCC)=O"),
# p-Nitrophenol
(("CCN", "CCC(OC1=CC=C([N+]([O-])=O)C=C1)=O"), "CCC(NCC)=O"),
# Pentafluorophenyl
(("CCN", "CCC(OC1=C(F)C(F)=C(F)C(F)=C1F)=O"), "CCC(NCC)=O"),
]
self._test_one_product(reactants, self.reactant_names)
# Those tests should not give any product.
def test_no_product(self):
reactants = [
# No primary amide
("NC(C)=O", "OC(C)=O"),
# No secondary amide
("CC(NC)=O", "OC(C)=O"),
# No N-methyl urea
("NC(NC)=O", "OC(C)=O"),
# No carbamates
("O=C(OC)NC", "OC(C)=O"),
# No imides
("CC(NC(C)=O)=O", "OC(C)=O"),
# No aniline
("NC1=CC=CC=C1", "OC(C1=CC=CC=C1)=O"),
# No tertiary amines
("CN(C)C", "OC(C)=O"),
# No guanosine
("NC(=N)N", "OC(C)=O")
]
self._test_no_product(reactants, self.reactant_names)
# This reactions should give multiple possible products
def test_if_get_products_returns_all_possible_products(self):
reactants = [
(("NCCNC", "OC(C)=O"), ("CNCCNC(C)=O", "NCCN(C(C)=O)C")),
(("CNCCNC", "OC(C)=O"), ("CNCCN(C)C(C)=O", "CNCCN(C)C(C)=O")),
(("N", "OC(CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O)=O"), ["OC(CN(CC(O)=O)CCN(CC(N)=O)CC(O)=O)=O"]*4),
]
self._test_all_possible_products(reactants, self.reactant_names)
def test_if_get_products_returns_only_1_products_if_symmetrical_as_one_is_true(self):
reactants = [
(("NCCNC", "OC(C)=O"), ["CNCCNC(C)=O", "NCCN(C(C)=O)C"]),
(("CNCCNC", "OC(C)=O"), ["CNCCN(C)C(C)=O"]),
(("N", "OC(CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O)=O"), ["OC(CN(CC(O)=O)CCN(CC(N)=O)CC(O)=O)=O"]),
]
self._test_all_possible_products(reactants, self.reactant_names, symmetrical_as_one=True)
def test_if_get_product_returns_the_symmetric_product_if_symmetrical_as_one_is_true(self):
reactants = [
(("CNCCNC", "OC(C)=O"), "CNCCN(C)C(C)=O"),
(("N", "OC(CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O)=O"), "OC(CN(CC(O)=O)CCN(CC(N)=O)CC(O)=O)=O"),
]
self._test_one_product(reactants, self.reactant_names, symmetrical_as_one=True)
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