Xylene and Toluene Degradation
Reaction212379
false
4-Methylcatechol + Oxygen ↔ 3-Methyl-cis,cis-muconate
REVERSIBLE
1.0
1.0
cis-1,2-Dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate
7470
PubChem-compound
C8H8O2
4-Methylbenzoic acid
136.05243
Reaction212491
false
3-Methyl-cis,cis-muconate ↔ 4-Methylmuconolactone
REVERSIBLE
Reaction212492
false
3-Methyl-cis,cis-muconate ↔ 3-Methylmuconolactone
REVERSIBLE
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
4-Methylcatechol
Reaction212495
false
1,2-Dihydroxy-3-methylcyclohexa-3,5-dienecarboxylate + NAD ↔ 3-Methylcatechol + Carbon dioxide + Hydrogen Ion + NADH
REVERSIBLE
CHEBI:10589 28795
ChEBI
Reaction212377
false
4-Methylbenzoic acid + Hydrogen Ion + NADH + Oxygen → NAD + cis-1,2-Dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate
LEFT_TO_RIGHT
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
HMDB0029635
HMDB
NADH
C7H8O4
4-Methylmuconolactone
156.04225
C7H8O4
3-Methylmuconolactone
156.04225
1.0
Cis-1,2-dihydroxycyclohexa-3,4-diene carboxylate dehydrogenase
439153
PubChem-compound
SMILES
CC1=CC(O)=C(O)C=C1
Probable ring-hydroxylating dioxygenase subunit
7190
ChemSpider
Q9I0W7
UniProt
Q9I0W5
UniProt
SMILES
CC1=CC(O)C(O)(C=C1)C(O)=O
Q9I0W4
UniProt
1.0
1.0
ReactionCatalysis202128
ACTIVATION
NAD
ReactionCatalysis202124
ACTIVATION
ReactionCatalysis202125
ACTIVATION
1.0
ReactionCatalysis202127
ACTIVATION
1.0
8953
PubChem-compound
8951
PubChem-compound
1.0
SMILES
C\C(\C=C/C(O)=O)=C\C(O)=O
5846
PubChem-compound
1.0
SMILES
CC1=C(C=CC=C1)C(O)=O
CHEBI:15846
ChEBI
Q9I232
UniProt
4-METHYLCATECHOL
BioCyc
Q9I0X5
UniProt
SMILES
CC1=CC=CC(O)C1(O)C(O)=O
Q9I0X3
UniProt
CHEBI:16754
ChEBI
SMILES
CC1=CC=C(C=C1)C(O)=O
9958
PubChem-compound
1038
PubChem-compound
388299
ChemSpider
Reaction212398
false
NAD + cis-1,2-Dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate ↔ 4-Methylcatechol + Carbon dioxide + Hydrogen Ion + NADH
REVERSIBLE
Reaction212399
false
Hydrogen Ion + NADH + Oxygen + o-Methylbenzoate ↔ 1,2-Dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate + NAD
REVERSIBLE
HMDB0001487
HMDB
952
ChemSpider
O2
Oxygen
31.98983
m-Methylbenzoate
1.0
274
ChemSpider
SMILES
CC1=CC(=CC=C1)C(O)=O
CHEBI:16908
ChEBI
C8H10O4
cis-1,2-Dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate
170.0579
9424
PubChem-compound
Toluate 1,2-dioxygenase
C06729
KEGG Compound
452-86-8
CAS
CHEBI:16766
ChEBI
CHEBI:16526
ChEBI
CHEBI:36635
ChEBI
1.0
9420
PubChem-compound
1010
ChemSpider
7782-44-7
CAS
HMDB0001377
HMDB
C7H8O4
3-Methyl-cis,cis-muconate
156.04225
o-Methylbenzoate
1,2-Dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate
C8H8O2
o-Methylbenzoate
136.05243
3-Methyl-cis,cis-muconate
C8H10O4
1,2-Dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate
170.0579
1.0
Hydrogen Ion
1.0
CHEBI:28958
ChEBI
CPD-6641
BioCyc
CO2
Carbon dioxide
43.98983
ReactionCatalysis202032
ACTIVATION
5893
PubChem-compound
C06730
KEGG Compound
9564
ChemSpider
58-68-4
CAS
C00080
KEGG Compound
SMILES
O=O
C8H8O2
m-Methylbenzoate
136.05243
Oxygen
124-38-9
CAS
Pseudomonas aeruginosa
CHEBI:18404
ChEBI
C00007
KEGG Compound
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
4-Methylbenzoic acid
ReactionCatalysis202048
ACTIVATION
ReactionCatalysis202049
ACTIVATION
C00004
KEGG Compound
C00003
KEGG Compound
C01454
KEGG Compound
CHEBI:16100
ChEBI
280
PubChem-compound
CHEBI:28872 36632
ChEBI
SMILES
CC1=CC=C[C@@](O)([C@H]1O)C(O)=O
Probable ring-hydroxylating dioxygenase subunit
SMILES
CC1=C(O)C(O)=CC=C1
Cis-1,2-dihydroxycyclohexa-3,4-diene carboxylate dehydrogenase
C21H27N7O14P2
NAD
663.10913
SMP0122466
SMPDB
C00011
KEGG Compound
SMILES
O=C=O
6802
PubChem-compound
HMDB0000902
HMDB
1.0
8943
PubChem-compound
ReactionCatalysis202131
ACTIVATION
CHEBI:17641
ChEBI
HMDB0000873
HMDB
SMILES
CC1=CC(=O)OC1CC(O)=O
PW123776
PathWhiz
Muconate cycloisomerase I
SMILES
CC1(CC(O)=O)OC(=O)C=C1
C21H29N7O14P2
NADH
665.12476
4-Methylmuconolactone
3-Methylmuconolactone
C7H8O2
4-Methylcatechol
124.05243
NADH
BioCyc
287
TAXONOMY
NAD
BioCyc
Reaction212488
false
1,2-Dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate + NAD → 3-Methylcatechol + Carbon dioxide + Hydrogen Ion + NADH
LEFT_TO_RIGHT
H
Hydrogen Ion
1.007825
Reaction212489
false
Hydrogen Ion + NADH + Oxygen + m-Methylbenzoate → 1,2-Dihydroxy-3-methylcyclohexa-3,5-dienecarboxylate + NAD
LEFT_TO_RIGHT
99-94-5
CAS
977
PubChem-compound
Catechol 1,2-dioxygenase
Toluate 1,2-dioxygenase beta subunit
HMDB0059597
HMDB
7163
PubChem-compound
Toluate 1,2-dioxygenase alpha subunit
7162
PubChem-compound
Carbon dioxide
HMDB0001967
HMDB
488-17-5
CAS
1.0
CHEBI:17095
ChEBI
1.0
ReactionCatalysis202028
ACTIVATION
53-84-9
CAS
CHEBI:17254
ChEBI
Catechol 1,2-dioxygenase
1,2-Dihydroxy-3-methylcyclohexa-3,5-dienecarboxylate
C7H8O2
3-Methylcatechol
124.05243
Toluate 1,2-dioxygenase alpha subunit
Toluate 1,2-dioxygenase beta subunit
C8H10O4
1,2-Dihydroxy-3-methylcyclohexa-3,5-dienecarboxylate
170.0579
Muconate cycloisomerase I
3-Methylcatechol