def test_gaunine_enumeration():
    """Gaunine tautomers"""
    assert enumerate_tautomers_smiles('N1C(N)=NC=2N=CNC2C1=O') == {
        'N=c1[nH]c(=O)c2[nH]cnc2[nH]1',
        'N=c1[nH]c(=O)c2nc[nH]c2[nH]1',
        'N=c1[nH]c2ncnc-2c(O)[nH]1',
        'N=c1nc(O)c2[nH]cnc2[nH]1',
        'N=c1nc(O)c2nc[nH]c2[nH]1',
        'N=c1nc2[nH]cnc2c(O)[nH]1',
        'N=c1nc2nc[nH]c2c(O)[nH]1',
        'Nc1nc(=O)c2[nH]cnc2[nH]1',
        'Nc1nc(=O)c2nc[nH]c2[nH]1',
        'Nc1nc(O)c2[nH]cnc2n1',
        'Nc1nc(O)c2nc[nH]c2n1',
        'Nc1nc(O)c2ncnc-2[nH]1',
        'Nc1nc2[nH]cnc2c(=O)[nH]1',
        'Nc1nc2nc[nH]c2c(=O)[nH]1',
        'Nc1nc2ncnc-2c(O)[nH]1'
    }

def test_1_5_aromatic_heteroatom_enumeration13():
    """1,5 aromatic heteroatom H shift"""
    eq_(enumerate_tautomers_smiles('CN=c1nc[nH]cc1'), {'CN=c1ccnc[nH]1', 'CNc1ccncn1', 'CN=c1cc[nH]cn1'})

def test_1_3_aromatic_heteroatom_enumeration3():
    """1,3 aromatic heteroatom H shift"""
    eq_(enumerate_tautomers_smiles('Oc1ncc[nH]1'), {'Oc1ncc[nH]1', 'O=c1[nH]cc[nH]1'})

def test_aliphatic_imine_enumeration2():
    """aliphatic imine tautomer"""
    eq_(enumerate_tautomers_smiles('C1(=CCCCC1)N'), {'N=C1CCCCC1', 'NC1=CCCCC1'})

def test_1_5_keto_enol_enumeration():
    """1,5 keto/enol tautomer"""
    eq_(enumerate_tautomers_smiles('Oc1nccc2cc[nH]c(=N)c12'), {'Nc1nccc2ccnc(O)c12', 'N=c1[nH]ccc2ccnc(O)c12', 'Nc1[nH]ccc2ccnc(=O)c1-2', 'Nc1nccc2cc[nH]c(=O)c12', 'N=c1[nH]ccc2cc[nH]c(=O)c12', 'N=c1nccc2cc[nH]c(O)c1-2'})

def test_keto_enol_enumeration():
    """keto/enol tautomer"""
    eq_(enumerate_tautomers_smiles('OC(C)=C(C)C'), {'C=C(O)C(C)C', 'CC(C)=C(C)O', 'CC(=O)C(C)C'})

def test_mobile_double_stereochemistry_enumeration():
    """Remove stereochemistry from mobile double bonds"""
    eq_(enumerate_tautomers_smiles('c1(ccccc1)/C=C(/O)\\C'), {'C=C(O)Cc1ccccc1', 'CC(O)=Cc1ccccc1', 'CC(=O)Cc1ccccc1'})

def test_acetone_keto_enol_enumeration2():
    """Enumerate acetone keto/enol tautomer."""
    eq_(enumerate_tautomers_smiles('CC(C)=O'), {'CC(C)=O', 'C=C(C)O'})

def test_heterocyclic_enumeration5():
    """heterocyclic tautomer"""
    eq_(enumerate_tautomers_smiles('c1cnc2ccc[nH]c12'), {'c1c[nH]c2ccnc-2c1', 'c1cnc2cc[nH]c2c1'})

def test_heterocyclic_enumeration4():
    """heterocyclic tautomer"""
    eq_(enumerate_tautomers_smiles('n1ccc2c[nH]ccc12'), {'c1cc2[nH]ccc2cn1', 'c1cc2c[nH]ccc-2n1'})

def test_heterocyclic_enumeration2():
    """heterocyclic tautomer"""
    eq_(enumerate_tautomers_smiles('c1cc(=O)[nH]c2nccn12'), {'O=c1ccn2cc[nH]c2n1', 'Oc1ccn2ccnc2n1', 'O=c1ccn2ccnc2[nH]1'})

def test_1_3_keto_enol_enumeration2():
    """Enumerate 1,3 keto/enol tautomer."""
    eq_(enumerate_tautomers_smiles('C1(CCCCC1)=O'), {'OC1=CCCCC1', 'O=C1CCCCC1'})

def test_1_11_aromatic_heteroatom_enumeration2():
    """1,11 aromatic heteroatom H shift"""
    eq_(enumerate_tautomers_smiles('N=C1C=CC(=Cc2ccc(O)cc2)C=C1'), {'Nc1ccc(C=C2C=CC(=O)C=C2)cc1', 'N=C1C=CC(=CC2C=CC(=O)C=C2)C=C1', 'N=C1C=CC(=Cc2ccc(O)cc2)C=C1', 'N=C1C=CC(C=C2C=CC(=O)C=C2)C=C1'})

def test_1_9_aromatic_heteroatom_enumeration2():
    """1,9 aromatic heteroatom H shift"""
    eq_(enumerate_tautomers_smiles('CN=c1ccnc2nc[nH]n21'), {'CN=c1ccnc2nc[nH]n12', 'CN=c1cc[nH]c2ncnn12', 'CN=c1ccnc2[nH]cnn12', 'CNc1ccnc2ncnn12'})

def test_1_7_aromatic_heteroatom_enumeration2():
    """1,7 aromatic heteroatom H shift"""
    eq_(enumerate_tautomers_smiles('c1ccc2c(c1)NC(=C1N=c3ccccc3=N1)N2'), {'C1=CC2=NC(C3N=c4ccccc4=N3)=NC2C=C1', 'C1=CC2=NC(c3nc4ccccc4[nH]3)=NC2C=C1', 'c1ccc2[nH]c(-c3nc4ccccc4[nH]3)nc2c1', 'C1=CC2=NC(=C3N=c4ccccc4=N3)NC2C=C1', 'c1ccc2c(c1)=NC(c1nc3ccccc3[nH]1)N=2', 'c1ccc2c(c1)NC(=C1N=c3ccccc3=N1)N2'})

def test_formamidinesulfinic_acid_enumeration2():
    """formamidinesulfinic acid tautomer"""
    eq_(enumerate_tautomers_smiles('N=C(N)S(=O)O'), {'N=C(N)S(=O)O', 'N[C](N)[S](=O)=O'})

def test_isocyanide_enumeration2():
    """isocyanide tautomer"""
    eq_(enumerate_tautomers_smiles('[C-]#[NH+]'), {'[C-]#[NH+]', 'C#N'})

def test_furanone_enumeration2():
    """furanone tautomer"""
    eq_(enumerate_tautomers_smiles('O=C1CC=CO1'), {'Oc1ccco1', 'O=C1CC=CO1'})

def test_phosphonic_acid_enumeration2():
    """phosphonic acid tautomer"""
    eq_(enumerate_tautomers_smiles('P(O)(O)O'), {'OP(O)O', 'O=[PH](O)O'})

def test_keten_ynol_enumeration2():
    """keten/ynol tautomer"""
    eq_(enumerate_tautomers_smiles('CC#CO'), {'CC=C=O', 'CC#CO'})