chython 2.19__cp313-cp313-win_amd64.whl

chython/algorithms/groups/test/test_reactions.py

@@ -0,0 +1,377 @@
+# -*- coding: utf-8 -*-
+#
+#  Copyright 2026 Ramil Nugmanov <nougmanoff@protonmail.com>
+#  This file is part of chython.
+#
+#  chython is free software; you can redistribute it and/or modify
+#  it under the terms of the GNU Lesser General Public License as published by
+#  the Free Software Foundation; either version 3 of the License, or
+#  (at your option) any later version.
+#
+#  This program is distributed in the hope that it will be useful,
+#  but WITHOUT ANY WARRANTY; without even the implied warranty of
+#  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+#  GNU Lesser General Public License for more details.
+#
+#  You should have received a copy of the GNU Lesser General Public License
+#  along with this program; if not, see <https://www.gnu.org/licenses/>.
+#
+import pytest
+from chython import smiles
+
+
+# (test_id, reaction_name, reaction_smiles, expected_count, exclude)
+# Reaction SMILES are parsed, canonicalized, then reactants are fed to @ operator.
+# expected_count: number of results from @ (2 for tautomeric azoles).
+# exclude: optional set of reaction names to filter from results (known overlaps).
+_two_component = [
+    ('amidation_acyl_chloride_primary_amine',
+     'amidation', 'ClC(=O)C.NCC>>CCNC(=O)C', 1),
+    ('suzuki_aryl_bromide_boronic_acid',
+     'suzuki', 'Brc1ccc(cc1)C.OB(O)c1ccccc1>>c1cc(ccc1-c1ccccc1)C', 1),
+    ('suzuki_alkenyl_boronic_acid',
+     'suzuki', 'Brc1ccc(cc1)C.OB(O)C=CC>>c1cc(ccc1C=CC)C', 1),
+    ('suzuki_alkyl_boronic_acid',
+     'suzuki', 'Brc1ccc(cc1)C.OB(O)CCC>>c1cc(ccc1CCC)C', 1),
+    ('buchwald_hartwig_aryl_bromide_primary_amine',
+     'buchwald_hartwig', 'Brc1ccc(cc1)C.NCC>>c1cc(ccc1C)NCC', 1),
+    ('buchwald_hartwig_pyridone_bromide_primary_amine',
+     'buchwald_hartwig', 'CN1C=CC(Br)=CC1=O.NCC>>CN1C=CC(=CC1=O)NCC', 1),
+    ('mitsunobu_ether_primary_alcohol_phenol',
+     'mitsunobu', 'OCC.Oc1ccc(cc1)C>>c1cc(ccc1C)OCC', 1),
+    ('mitsunobu_ester_primary_alcohol_acid',
+     'mitsunobu', 'OCC.OC(=O)c1ccccc1>>c1ccccc1C(OCC)=O', 1),
+    ('deoxygenative_coupling_alcohol_aryl_bromide',
+     'deoxygenative_coupling', 'OCC.Brc1ccc(cc1)C>>c1cc(ccc1C)CC', 1, {'snar'}),
+    ('decarboxylative_coupling_acid_aryl_bromide',
+     'decarboxylative_coupling', 'OC(=O)CC.Brc1ccc(cc1)C>>c1cc(ccc1C)CC', 1),
+    ('xec_aryl_bromide_alkyl_bromide',
+     'xec', 'Brc1ccc(cc1)C.BrCCC>>c1cc(ccc1CCC)C', 1),
+    ('reductive_amination_aldehyde_primary_amine',
+     'reductive_amination', 'O=CC.NCc1ccccc1>>c1cc(ccc1)CNCC', 1),
+    ('reductive_amination_ketone_secondary_amine',
+     'reductive_amination', 'O=C(C)C.N(C)CC>>CC(C)N(C)CC', 1),
+    ('ullmann_phenol_aryl_bromide_cresol',
+     'ullmann_phenol', 'Brc1ccc(cc1)C.Oc1ccc(cc1)CC>>c1cc(ccc1C)Oc1ccc(cc1)CC', 1),
+    ('ullmann_pyrrole_aryl_bromide_pyrrole',
+     'ullmann_pyrrole', 'Brc1ccc(cc1)C.[nH]1cccc1>>c1ccn(c1)-c1ccc(cc1)C', 1),
+    ('ullmann_pyrrole_aryl_bromide_pyrazole',
+     'ullmann_pyrrole', 'Brc1ccc(cc1)C.[nH]1nccc1>>c1cc(ccc1-n1nccc1)C', 2),
+    ('ullmann_pyrrole_aryl_bromide_imidazole',
+     'ullmann_pyrrole', 'Brc1ccc(cc1)C.[nH]1cncc1>>c1cc(ccc1-n1ccnc1)C', 2),
+    ('ullmann_pyrrole_pyridone_chloride_pyrrole',
+     'ullmann_pyrrole', 'CN1C=CC(Cl)=CC1=O.[nH]1cccc1>>CN1C=CC(=CC1=O)-n1cccc1', 1),
+    ('chan_lam_boronic_acid_primary_amine',
+     'chan_lam', 'OB(O)c1ccc(cc1)C.NCC>>c1cc(ccc1C)NCC', 1),
+    ('chan_lam_boronic_acid_phenol',
+     'chan_lam', 'OB(O)c1ccc(cc1)C.Oc1ccc(cc1)CC>>c1cc(ccc1C)Oc1ccc(cc1)CC', 1),
+    ('sulfonylation_sulfonyl_chloride_alcohol',
+     'sulfonylation', 'ClS(=O)(=O)c1ccccc1.OCCC>>c1ccccc1S(=O)(=O)OCCC', 1),
+    ('sulfonamide_formation_sulfonyl_chloride_amine',
+     'sulfonamide_formation', 'ClS(=O)(=O)c1ccccc1.NCC>>c1ccccc1S(=O)(=O)NCC', 1),
+    ('aminolysis_ester_primary_amine',
+     'aminolysis', 'COC(=O)c1ccc(cc1)C.NCC>>c1cc(ccc1C(NCC)=O)C', 1),
+    ('grignard_alkyl_bromide_aldehyde',
+     'grignard', 'BrCC.O=Cc1ccc(cc1)C>>c1cc(ccc1C)C(CC)O', 1),
+    ('grignard_alkyl_bromide_ketone',
+     'grignard', 'BrCC.O=C(C)c1ccccc1>>c1cc(ccc1)C(O)(C)CC', 1),
+    ('sonogashira_aryl_bromide_terminal_alkyne',
+     'sonogashira', 'Brc1ccc(cc1)C.C#CC>>c1cc(ccc1C)C#CC', 1),
+    ('urea_synthesis_isocyanate_primary_amine',
+     'urea_synthesis', 'O=C=Nc1ccccc1.NCC>>c1ccccc1NC(NCC)=O', 1),
+    ('cuaac_azide_terminal_alkyne',
+     'cuaac', 'CC#C.CN=[N+]=[N-]>>Cc1cn(C)nn1', 1),
+    ('snar_aryl_fluoride_primary_amine',
+     'snar', 'Fc1ccc(cc1)C(F)(F)F.NCC>>c1cc(ccc1C(F)(F)F)NCC', 1),
+    ('snar_aryl_fluoride_phenol',
+     'snar', 'Fc1ccc(cc1)C(F)(F)F.Oc1ccc(cc1)C>>c1cc(ccc1C(F)(F)F)Oc1ccc(cc1)C', 1),
+    ('snar_aryl_fluoride_thiol',
+     'snar', 'Fc1ccc(cc1)C(F)(F)F.SCC>>c1cc(ccc1C(F)(F)F)SCC', 1),
+    ('williamson_alkyl_bromide_phenol',
+     'williamson', 'BrCC.Oc1ccc(cc1)C>>c1cc(ccc1C)OCC', 1),
+    ('williamson_alkyl_bromide_alcohol',
+     'williamson', 'BrCCC.OCC>>CCCOCC', 1),
+    ('williamson_mesylate_phenol',
+     'williamson', 'CS(=O)(=O)OCC.Oc1ccc(cc1)C>>c1cc(ccc1C)OCC', 1),
+    ('williamson_triflate_alcohol',
+     'williamson', 'FC(F)(F)S(=O)(=O)OCC.OCCC>>CCCOCC', 1),
+    ('acylation_acyl_chloride_alcohol',
+     'acylation', 'ClC(=O)c1ccccc1.OCC>>c1ccccc1C(OCC)=O', 1),
+    ('thioether_thiol_alkyl_bromide',
+     'thioether', 'SCC.BrCCC>>CCSCCC', 1),
+    ('carbamate_isocyanate_alcohol',
+     'carbamate', 'O=C=Nc1ccccc1.OCC>>c1ccccc1NC(OCC)=O', 1),
+    ('tetrazole_azide_nitrile',
+     'tetrazole', 'CN=[N+]=[N-].N#Cc1ccccc1>>c1ccc(cc1)-c1nnn(C)n1', 1),
+    ('kumada_aryl_bromide_alkyl_grignard',
+     'kumada', 'Brc1ccc(cc1)C.C[Mg]Br>>c1cc(ccc1C)C', 1),
+    ('kumada_aryl_bromide_aryl_grignard',
+     'kumada', 'Brc1ccc(cc1)C.c1ccccc1[Mg]Br>>c1cc(ccc1-c1ccccc1)C', 1),
+    ('negishi_aryl_bromide_alkyl_zinc',
+     'negishi', 'Brc1ccc(cc1)C.CC[Zn]Cl>>c1cc(ccc1C)CC', 1),
+    ('stille_aryl_bromide_aryl_stannane',
+     'stille', 'Brc1ccc(cc1)C.c1ccccc1[Sn](C)(C)C>>c1cc(ccc1-c1ccccc1)C', 1),
+    ('stille_aryl_bromide_alkenyl_stannane',
+     'stille', 'Brc1ccc(cc1)C.C=C[Sn](C)(C)C>>c1cc(ccc1C=C)C', 1),
+    ('hiyama_aryl_bromide_aryl_silane',
+     'hiyama', 'Brc1ccc(cc1)C.c1ccccc1[Si](C)(C)C>>c1cc(ccc1-c1ccccc1)C', 1),
+    ('grignard_explicit_alkyl_grignard_aldehyde',
+     'grignard', 'CC[Mg]Br.O=Cc1ccccc1>>c1ccccc1C(CC)O', 1),
+    ('nitrile_grignard_alkyl',
+     'nitrile_grignard', 'N#CCC.CC[Mg]Br>>CCC(=O)CC', 1),
+    ('heck_aryl_bromide_terminal_alkene',
+     'heck', 'Brc1ccc(cc1)C.C=CC>>c1cc(ccc1C=CC)C', 1),
+    ('heck_aryl_bromide_internal_alkene',
+     'heck', 'Brc1ccccc1.CC=CC>>c1ccccc1C(C)=CC', 1),
+    ('cross_metathesis_two_terminal_alkenes',
+     'cross_metathesis', 'C=CC.C=CCCC>>CC=CCCC', 1),
+    ('wittig_ylide_aldehyde',
+     'wittig', 'c1ccccc1P(c1ccccc1)(c1ccccc1)=C.c1cc(ccc1C=O)C>>c1cc(ccc1C)C=C', 1),
+    ('hwe_phosphonate_aldehyde',
+     'hwe', 'CCP(=O)(OC)OC.c1cc(ccc1C=O)C>>c1cc(ccc1C=CC)C', 1),
+    ('weinreb_explicit_grignard',
+     'weinreb', 'CC(=O)N(C)OC.CC[Mg]Br>>CCC(=O)C', 1),
+    ('weinreb_ester_surrogate_grignard',
+     'weinreb', 'COC(=O)c1ccccc1.CC[Mg]Br>>c1ccccc1C(=O)CC', 1),
+    ('weinreb_acyl_chloride_surrogate_grignard',
+     'weinreb', 'c1ccccc1C(=O)Cl.CC[Mg]Br>>c1ccccc1C(=O)CC', 1),
+    ('friedel_crafts_acyl_chloride_benzene',
+     'friedel_crafts', 'CC(=O)Cl.c1ccccc1>>c1ccccc1C(=O)C', 1),
+    ('hantzsch_thiazole_chloroacetone_thioacetamide',
+     'hantzsch_thiazole', 'ClCC(=O)C.NC(=S)C>>c1(C)scc(C)n1', 1),
+    ('knorr_pyrazole_acetylacetone_methylhydrazine',
+     'knorr_pyrazole', 'O=C(C)CC(=O)C.NNC>>c1(C)nn(c(C)c1)C', 1),
+    ('paal_knorr_hexanedione_ethylamine',
+     'paal_knorr', 'O=C(C)CCC(=O)C.NCC>>Cc1ccc(C)n1CC', 1, {'reductive_amination'}),
+    ('fischer_indole_phenylhydrazine_acetone',
+     'fischer_indole', 'NNc1ccccc1.O=C(C)C>>c1cc2c(cc(C)[nH]2)cc1', 1, {'hydrazone'}),
+    ('benzimidazole_diamine_aldehyde',
+     'benzimidazole', 'Nc1ccccc1N.O=CC>>c1(C)[nH]c2c(cccc2)n1', 1, {'reductive_amination'}),
+    ('benzoxazole_aminophenol_aldehyde',
+     'benzoxazole', 'Nc1ccccc1O.O=CC>>c1cccc2nc(oc12)C', 1, {'reductive_amination'}),
+    ('benzothiazole_aminothiophenol_aldehyde',
+     'benzothiazole', 'Nc1ccccc1S.O=CC>>Cc1nc2c(s1)cccc2', 1, {'reductive_amination'}),
+    ('quinoxaline_diamine_diketone',
+     'quinoxaline', 'Nc1ccccc1N.O=C(C)C(=O)C>>c12c(nc(c(n1)C)C)cccc2', 1, {'reductive_amination'}),
+    ('friedlander_aminobenzaldehyde_acetone',
+     'friedlander', 'Nc1ccccc1C=O.O=C(C)C>>n1c2c(ccc1C)cccc2', 1, {'reductive_amination', 'aldol'}),
+    ('pictet_spengler_phenethylamine_aldehyde',
+     'pictet_spengler', 'NCCc1ccccc1.O=CC>>N1CCc2ccccc2C1C', 1, {'reductive_amination'}),
+    ('oxadiazole_124_amidoxime_acyl_chloride',
+     'oxadiazole_124', 'N=C(NO)C.ClC(=O)C>>c1(C)noc(n1)C', 1),
+    ('pyrimidine_diketone_amidine',
+     'pyrimidine', 'O=C(C)CC(=O)C.NC(=N)C>>Cc1nc(nc(C)c1)C', 1),
+    ('van_leusen_oxazole_tosmic_aldehyde',
+     'van_leusen_oxazole', '[C-]#[N+]CS(=O)(=O)c1ccc(cc1)C.O=CC>>c1oc(C)nc1', 1),
+    ('imidazopyridine_aminopyridine_haloketone',
+     'imidazopyridine', 'Nc1ncccc1.ClCC(=O)C>>c1cccn2c1nc(C)c2', 1, {'reductive_amination', 'n_alkylation'}),
+    ('niementowski_anthranilic_acid_amide',
+     'niementowski', 'Nc1ccccc1C(=O)O.NC(=O)C>>Oc1c2c(nc(n1)C)cccc2', 1),
+    ('liebeskind_srogl_thioester_boronic_acid',
+     'liebeskind_srogl', 'O=C(SC)c1ccccc1.OB(O)c1ccccc1>>O=C(c1ccccc1)c1ccccc1', 1),
+    ('knoevenagel_malononitrile_aldehyde',
+     'knoevenagel', 'N#CCC#N.O=Cc1ccccc1>>c1cc(ccc1)C=C(C#N)C#N', 1),
+    ('aldol_acetone_benzaldehyde',
+     'aldol', 'O=C(C)C.O=Cc1ccccc1>>c1cc(ccc1)C(CC(=O)C)O', 1, {'reductive_amination'}),
+    ('larock_indole_bromoaniline_butyne',
+     'larock_indole', 'Nc1ccccc1Br.CC#CC>>Cc1[nH]c2c(cccc2)c1C', 1, {'reductive_amination'}),
+    ('doebner_miller_aniline_crotonaldehyde',
+     'doebner_miller', 'Nc1ccccc1.O=CC=CC>>C1=CC=CC=2C(C)=CC=NC12', 1, {'reductive_amination'}),
+]
+
+_three_component = [
+    ('ugi_3cr_aldehyde_amine_isocyano',
+     'ugi_3cr', 'O=CC.NCC.[C-]#[N+]C>>CCNC(C(=O)NC)C', 1),
+    ('biginelli_aldehyde_ketoester_urea',
+     'biginelli', 'O=CC.O=C(C)CC(=O)OC.NC(=O)N>>N1C(NC(C)C=C1C)=O', 1),
+    ('hantzsch_pyridine_aldehyde_ketoester',
+     'hantzsch_pyridine', 'O=CC.O=C(C)CC(=O)OCC.O=C(C)CC(=O)OCC>>c1(C)c(c(nc(c1C(=O)OCC)C)C)C(=O)OCC', 1),
+]
+
+_four_component = [
+    ('ugi_4cr_aldehyde_amine_acid_isocyano',
+     'ugi_4cr', 'O=CC.NCC.OC(=O)C.[C-]#[N+]C>>N(CC)(C(C(NC)=O)C)C(C)=O', 1),
+]
+
+_transformations = [
+    ('isoxazole_from_diketone', 'isoxazole', 'O=C(C)CC(=O)C>>c1(onc(C)c1)C', 1,
+     {'alpha_halogenation', 'oximation', 'oxo_to_difluoro', 'oxo_to_thioxo'}),
+    ('pyridazine_from_diketone', 'pyridazine', 'O=C(C)CCC(=O)C>>c1(C)nnc(C)cc1', 1,
+     {'alpha_halogenation', 'oximation', 'oxo_to_difluoro', 'oxo_to_thioxo'}),
+    ('appel_primary_alcohol', 'appel', 'OCC>>BrCC', 1,
+     {'triflation', 'appel_chloride', 'mesylation', 'tosylation', 'fluorination', 'appel_iodide', 'azidation'}),
+    ('appel_secondary_alcohol', 'appel', 'OC(C)CC>>BrC(C)CC', 1,
+     {'triflation', 'appel_chloride', 'mesylation', 'tosylation', 'fluorination', 'appel_iodide', 'azidation'}),
+    ('borylation_aryl_bromide', 'borylation_acid', 'Brc1c(C)c(C)c(C)c(C)c1C>>OB(O)c1c(C)c(C)c(C)c(C)c1C', 1,
+     {'borylation_ester', 'cyanation', 'halide_hydrolysis', 'azidation', 'finkelstein', 'halex',
+      'halide_to_chloride', 'halide_to_methoxy', 'halide_to_thioether', 'halide_to_thiol'}),
+    ('nitrile_hydrolysis', 'nitrile_hydrolysis', 'N#CCC>>NC(=O)CC', 1, {'nitrile_to_acid'}),
+    ('nitration_benzene', 'nitration', 'c1ccccc1>>[O-][N+](=O)c1ccccc1', 1,
+     {'bromination', 'chlorination', 'iodination', 'fluorination'}),
+    ('bromination_benzene', 'bromination', 'c1ccccc1>>Brc1ccccc1', 1,
+     {'nitration', 'chlorination', 'iodination', 'fluorination'}),
+    ('chlorination_benzene', 'chlorination', 'c1ccccc1>>Clc1ccccc1', 1,
+     {'nitration', 'bromination', 'iodination', 'fluorination'}),
+    ('iodination_benzene', 'iodination', 'c1ccccc1>>Ic1ccccc1', 1,
+     {'nitration', 'bromination', 'chlorination', 'fluorination'}),
+]
+
+_oxidations = [
+    ('alcohol_to_aldehyde', 'alcohol_to_aldehyde', 'OCC>>O=CC', 1),
+    ('alcohol_to_ketone', 'alcohol_to_ketone', 'OC(C)C>>O=C(C)C', 1),
+    ('aldehyde_to_acid', 'aldehyde_to_acid', 'O=CC>>OC(=O)C', 1),
+    ('dihydroxylation', 'dihydroxylation', 'C=Cc1ccccc1>>OC(CO)c1ccccc1', 1),
+    ('thioether_to_sulfoxide', 'thioether_to_sulfoxide', 'CSC>>CS(=O)C', 1, {'thioether_to_sulfone'}),
+    ('thioether_to_sulfone', 'thioether_to_sulfone', 'CSC>>CS(=O)(=O)C', 1, {'thioether_to_sulfoxide'}),
+    ('sulfoxide_to_sulfone', 'sulfoxide_to_sulfone', 'CS(=O)C>>CS(=O)(=O)C', 1),
+]
+
+_reductions = [
+    ('aldehyde_to_alcohol', 'aldehyde_to_alcohol', 'O=Cc1ccccc1>>OCc1ccccc1', 1, {'carbonyl_to_amine'}),
+    ('ketone_to_alcohol', 'ketone_to_alcohol', 'O=C(C)c1ccccc1>>OC(C)c1ccccc1', 1, {'carbonyl_to_amine'}),
+    ('acid_to_alcohol', 'acid_to_alcohol', 'OC(=O)c1ccccc1>>OCc1ccccc1', 1),
+    ('ester_to_alcohol', 'ester_to_alcohol', 'COC(=O)c1ccccc1>>OCc1ccccc1', 1),
+    ('amide_to_amine_primary', 'amide_to_amine', 'NC(=O)c1ccccc1>>NCc1ccccc1', 1),
+    ('amide_to_amine_secondary', 'amide_to_amine', 'CNC(=O)c1ccccc1>>CNCc1ccccc1', 1),
+    ('nitrile_to_amine', 'nitrile_to_amine', 'N#Cc1ccccc1>>NCc1ccccc1', 1),
+    ('nitro_to_amine', 'nitro_to_amine', '[O-][N+](=O)c1ccccc1>>Nc1ccccc1', 1),
+    ('azide_to_amine', 'azide_to_amine', 'CN=[N+]=[N-]>>CN', 1),
+    ('deoxygenation_primary', 'deoxygenation', 'OCC1CCCCC1>>CC1CCCCC1', 1),
+    ('deoxygenation_secondary', 'deoxygenation', 'OC(C)c1ccccc1>>CCc1ccccc1', 1),
+]
+
+
+@pytest.mark.parametrize(
+    'args',
+    _two_component,
+    ids=[x[0] for x in _two_component]
+)
+def test_two_component(args):
+    test_id, rxn_name, rxn_smi, expected_count = args[:4]
+    exclude = args[4] if len(args) > 4 else set()
+
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    r1, r2 = r.reactants
+
+    results = [(n, rxn) for n, rxn in r1 @ r2 if n not in exclude]
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'
+
+
+@pytest.mark.parametrize(
+    'test_id,rxn_name,rxn_smi,expected_count',
+    _three_component,
+    ids=[x[0] for x in _three_component]
+)
+def test_three_component(test_id, rxn_name, rxn_smi, expected_count):
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    r1, r2, r3 = r.reactants
+
+    results = list(r1 @ [r2, r3])
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'
+
+
+@pytest.mark.parametrize(
+    'test_id,rxn_name,rxn_smi,expected_count',
+    _four_component,
+    ids=[x[0] for x in _four_component]
+)
+def test_four_component(test_id, rxn_name, rxn_smi, expected_count):
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    r1, r2, r3, r4 = r.reactants
+
+    results = list(r1 @ [r2, r3, r4])
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'
+
+
+@pytest.mark.parametrize(
+    'args',
+    _oxidations,
+    ids=[x[0] for x in _oxidations]
+)
+def test_oxidation(args):
+    test_id, rxn_name, rxn_smi, expected_count = args[:4]
+    exclude = args[4] if len(args) > 4 else set()
+
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    mol = r.reactants[0]
+
+    results = [(n, rxn) for n, rxn in mol.oxidize() if n not in exclude]
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'
+
+
+@pytest.mark.parametrize(
+    'args',
+    _reductions,
+    ids=[x[0] for x in _reductions]
+)
+def test_reduction(args):
+    test_id, rxn_name, rxn_smi, expected_count = args[:4]
+    exclude = args[4] if len(args) > 4 else set()
+
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    mol = r.reactants[0]
+
+    results = [(n, rxn) for n, rxn in mol.reduce() if n not in exclude]
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'
+
+
+@pytest.mark.parametrize(
+    'args',
+    _transformations,
+    ids=[x[0] for x in _transformations]
+)
+def test_transformation(args):
+    test_id, rxn_name, rxn_smi, expected_count = args[:4]
+    exclude = args[4] if len(args) > 4 else set()
+
+    r = smiles(rxn_smi)
+    r.canonicalize()
+    mol = r.reactants[0]
+
+    results = [(n, rxn) for n, rxn in mol.transform() if n not in exclude]
+
+    names = set(n for n, _ in results)
+    assert names == {rxn_name}, f'expected {rxn_name}, got {sorted(names)}'
+
+    assert len(results) == expected_count, f'expected {expected_count}, got {len(results)}'
+
+    for _, rxn in results:
+        assert rxn == r, f'expected {r}, got {rxn}'