SMILES
[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(=O)CC=CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
46926262
PubChem-compound
7722-84-1
CAS
17215925
ChemSpider
SMILES
O[C@H](C(C)(C)COP(=O)(O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(=O)NCCC(=O)NCCSC(=O)\C=C1\CC=CC=CO1
1.0
SMILES
O=CC\C([H])=C(\[H])CC(=O)CC(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=O
C23H38N7O17P3S
Acetyl-CoA
809.1258
SMILES
[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC12OC1([H])C=CC=C2)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
439161
PubChem-compound
937
ChemSpider
6.0
NADH
Protein maoC
C05332
KEGG Compound
HMDB0003125
HMDB
1.0
439153
PubChem-compound
SMILES
O
SMILES
OO
C10H14N5O7P
Adenosine monophosphate
347.06308
Pyrophosphate
1.0
1.0
CHEBI:16027
ChEBI
34-DIHYDROXYPHENYLACETYL-COA
BioCyc
NAD
HMDB0000538
HMDB
ATP
BioCyc
Phenylacetic acid degradation protein paaB
1001
PubChem-compound
H4N
Ammonium
18.034374
Phenylacetic acid degradation protein paaA
1.0
6816
PubChem-compound
C07086
KEGG Compound
559142
ChemSpider
53377481
PubChem-compound
CHEBI:15846
ChEBI
13876539
ChemSpider
Transport491
false
Phenylacetaldehyde (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol
LEFT_TO_RIGHT
53-59-8
CAS
1.0
CHEBI:15380
ChEBI
5742
ChemSpider
1038
PubChem-compound
C25H40N7O19P3S
Succinyl-CoA
867.1312
CHEBI:16474
ChEBI
952
ChemSpider
SMP0002041
SMPDB
GO:0005829
GENE ONTOLOGY
1.0
Adenosine monophosphate
C8H8O2
Phenylacetic acid
136.05243
HYDRPHENYLAC-CPD
BioCyc
CHEBI:16908
ChEBI
5858
ChemSpider
1.0
Acetyl-CoA
CHEBI:16240
ChEBI
C00582
KEGG Compound
NADPH
1010
ChemSpider
C8H8O
Phenylacetaldehyde
120.05752
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
Phenylacetaldehyde
1.0
NADP
PPI
BioCyc
C21H30N7O17P3
NADPH
745.0911
56927776
PubChem-compound
C21H29N7O17P3
NADP
744.08325
Phenylacetic acid degradation protein paaC
Phenylacetaldehyde dehydrogenase
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O
1.0
1.0
P76085
UniProt
NADPH
BioCyc
Ammonium
P76083
UniProt
Hydrogen Ion
P76081
UniProt
P76082
UniProt
Probable 3-hydroxybutyryl-CoA dehydrogenase
C8H11N
Phenylethylamine
121.08915
Phenylacetate-coenzyme A ligase
Cytosol
Probable phenylacetic acid degradation NADH oxidoreductase paaE
CPD-6641
BioCyc
HMDB0000209
HMDB
Probable enoyl-CoA hydratase paaF
218
ChemSpider
Adenosine triphosphate
58-68-4
CAS
165620
PubChem-compound
HMDB0001423
HMDB
SMILES
OC(=O)CC1=CC=CC=C1
HMDB0000217
HMDB
Oxygen
3.3.2.12
false
3.3.2.12
2-Oxepin-2(3H)-ylideneacetyl-CoA + Water → 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
LEFT_TO_RIGHT
Beta-ketoadipyl-CoA thiolase
P76077
UniProt
C00007
KEGG Compound
2,3-didehydroadipyl-CoA
C00006
KEGG Compound
CHEBI:15537
ChEBI
CHEBI:18009
ChEBI
C00001
KEGG Compound
predicted ring 1,2-epoxyphenylacetyl-CoA isomerase (oxepin-CoA forming)
3-Oxoadipyl-CoA
CHEBI:18361
ChEBI
ring 1,2-phenylacetyl-CoA epoxidase
C00005
KEGG Compound
C00004
KEGG Compound
Protein maoC
C00003
KEGG Compound
C00002
KEGG Compound
phenylacetaldehyde dehydrogenase
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
HMDB0000221
HMDB
copper-containing amine oxidase
SMILES
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
SMILES
O=CCC1=CC=CC=C1
P76078
UniProt
P76079
UniProt
PW002027
PathWhiz
53-57-6
CAS
C27H37N7O19P3S
2,3-didehydroadipyl-CoA
888.11053
C21H28N7O14P2
NAD
664.11694
1.0
C01342
KEGG Compound
CHEBI:28938
ChEBI
C00010
KEGG Compound
Primary amine oxidase
HMDB0000902
HMDB
C28H44N7O19P3S
3-Oxoadipyl-CoA
907.16254
Phenylacetic acid degradation protein paaA
C00013
KEGG Compound
O7P2
Pyrophosphate
173.91193
PHENYLACETATE
BioCyc
C21H29N7O14P2
NADH
665.12476
NAD(P)
BioCyc
PaaF-PaaG hydratase-isomerase complex
5957
PubChem-compound
HMDB0001206
HMDB
GO:0005620
GENE ONTOLOGY
CHEBI:63458
ChEBI
56928138
PubChem-compound
562
TAXONOMY
H
Hydrogen Ion
1.007825
3-Hydroxyadipyl-CoA
388307
ChemSpider
56-65-5
CAS
53-84-9
CAS
C00020
KEGG Compound
C00027
KEGG Compound
13856352
ChemSpider
Phenylethylamine
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1
C00024
KEGG Compound
Phenylacetic acid degradation protein paaC
1.0
1.0
1.0
C27H44N7O20P3S
3-Hydroxyadipyl-CoA
911.1575
1.0
P80668
UniProt
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
Probable enoyl-CoA hydratase paaG
CHEBI:18397
ChEBI
5682
ChemSpider
SMILES
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
CHEBI:1146900
ChEBI
Beta-ketoadipyl-CoA thiolase
Water
Hydrogen peroxide
AMP
BioCyc
ReactionCatalysis5889
ACTIVATION
ReactionCatalysis5888
ACTIVATION
HYDROGEN-PEROXIDE
BioCyc
2.0
ReactionCatalysis5883
ACTIVATION
ReactionCatalysis5882
ACTIVATION
ReactionCatalysis5881
ACTIVATION
HMDB0006236
HMDB
10181341
ChemSpider
ReactionCatalysis5887
ACTIVATION
HMDB0000250
HMDB
ReactionCatalysis5886
ACTIVATION
SMILES
[O-]P([O-])(=O)OP([O-])([O-])=O
ReactionCatalysis5885
ACTIVATION
14000-31-8
CAS
ReactionCatalysis5884
ACTIVATION
2-Oxepin-2(3H)-ylideneacetyl-CoA
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
C00601
KEGG Compound
CHEBI:16424
ChEBI
999
PubChem-compound
ReactionCatalysis5890
ACTIVATION
Phenylacetaldehyde
Phenylacetate-coenzyme A ligase
CO-A
BioCyc
Probable 3-hydroxybutyryl-CoA dehydrogenase
998
PubChem-compound
Probable enoyl-CoA hydratase paaF
Probable phenylacetic acid degradation NADH oxidoreductase paaE
P46883
UniProt
5675
ChemSpider
3-Oxo-5,6-dehydrosuberyl-CoA
72-89-9
CAS
Phenylacetaldehyde
Coenzyme A
1.0
763
ChemSpider
C21H36N7O16P3S
Coenzyme A
767.11523
1.0
604-98-8
CAS
14798-03-9
CAS
784
PubChem-compound
C29H44N7O19P3S
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
919.16254
CHEBI:15422
ChEBI
C29H42N7O18P3S
2-Oxepin-2(3H)-ylideneacetyl-CoA
901.152
C29H42N7O18P3S
2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
901.152
6557
ChemSpider
C29H44N7O20P3S
3-Oxo-5,6-dehydrosuberyl-CoA
935.1575
1.4.3.21
false
1.4.3.21
Oxygen + Phenylethylamine + Water → Ammonium + Hydrogen peroxide + Phenylacetaldehyde
LEFT_TO_RIGHT
7532-39-0
CAS
Escherichia coli
1.2.1.39
false
1.2.1.39
NAD + Phenylacetaldehyde + Water → Hydrogen Ion + NADH + Phenylacetic acid
LEFT_TO_RIGHT
6.2.1.30
false
6.2.1.30
Adenosine triphosphate + Coenzyme A + Phenylacetic acid → Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
LEFT_TO_RIGHT
SMILES
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
7732-18-5
CAS
388299
ChemSpider
HMDB0001487
HMDB
61-19-8
CAS
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
O2
Oxygen
31.98983
1.0
2.0
SMILES
[NH4+]
C10H16N5O13P3
Adenosine triphosphate
506.99576
64-04-0
CAS
1.0
Primary amine oxidase
1.0
7782-44-7
CAS
1.0
HMDB0001377
HMDB
HMDB0000045
HMDB
P77467
UniProt
962
PubChem-compound
SMILES
[H]\C(CCC([O-])=O)=C(/[H])C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O
392413
ChemSpider
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OCC1CC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)CCC(O)=O
Phenylacetic acid
HMDB0012275
HMDB
5893
PubChem-compound
C00080
KEGG Compound
SMILES
O=O
Periplasmic Space
Phenylacetic acid degradation protein paaB
HMDB0002111
HMDB
P77455
UniProt
HMDB0001022
HMDB
CHEBI:15377
ChEBI
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
Succinyl-CoA
Probable enoyl-CoA hydratase paaG
CHEBI:15490
ChEBI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C29H42N7O17P3S
Phenylacetyl-CoA
885.15704
5886
PubChem-compound
90
PubChem-compound
1.0
1.-.-.-
false
1.-.-.-
Hydrogen Ion + NADPH + Oxygen + Phenylacetyl-CoA → 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
LEFT_TO_RIGHT
ReactionCatalysis5857
ACTIVATION
C00091
KEGG Compound
1.0
5.3.3.18
false
5.3.3.18
2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA → 2-Oxepin-2(3H)-ylideneacetyl-CoA
LEFT_TO_RIGHT
Reaction5922
false
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water → 3-Oxo-5,6-dehydrosuberyl-CoA + Hydrogen Ion + NADPH
LEFT_TO_RIGHT
2.3.1.174
false
2.3.1.174
3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A → 2,3-didehydroadipyl-CoA + Acetyl-CoA
LEFT_TO_RIGHT
5.3.3.18
false
5.3.3.18
2,3-didehydroadipyl-CoA + Water → 3-Hydroxyadipyl-CoA
LEFT_TO_RIGHT
CHEBI:30745
ChEBI
1.1.1.-
false
1.1.1.-
3-Hydroxyadipyl-CoA + NAD → 3-Oxoadipyl-CoA + Hydrogen Ion + NADH
LEFT_TO_RIGHT
Reaction5926
false
3-Oxoadipyl-CoA + Coenzyme A → Acetyl-CoA + Succinyl-CoA
LEFT_TO_RIGHT
1.0
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CC(O)CCC(O)=O
644102
PubChem-compound
444493
PubChem-compound
6083
PubChem-compound
PHENYLETHYLAMINE
BioCyc
16741146
PubChem-compound
1.0
6.0
122-78-1
CAS
103-82-2
CAS
SMILES
NCCC1=CC=CC=C1
Phenylacetyl-CoA
22833512
PubChem-compound
ACETYL-COA
BioCyc
H2O
Water
18.010565
H2O2
Hydrogen peroxide
34.005478
1.0
NADH
BioCyc
3-METHYLBENZYLSUCCINYL-COA
BioCyc
NAD
BioCyc
46926194
PubChem-compound
Phenylacetaldehyde dehydrogenase
977
PubChem-compound
HMDB0041827
HMDB
HMDB0059597
HMDB
CHEBI:15351
ChEBI
145148
ChemSpider
1.0
HMDB0006503
HMDB
Phenylethylamine Metabolism
85-61-0
CAS
P0C7L2
UniProt