|
|
Toluene + reduced_ferredoxin_[iron-sulfur]_cluster + O2 + H+ <=> benzyl_alcohol + oxidized_ferredoxin + H2O
|
1.14.13
1.14.15.26
toluene methyl-monooxygenase
|
–
–
|
| |
BRENDA:
BR52308
KEGG:
R02550
MetaCyc:
TOLUENE-SIDE-CHAIN-MONOOXYGENASE-RXN
|
|
|
|
benzaldehyde + H2O + NADP+ <=> benzoate + NADPH + H+
|
1.1.1.195
cinnamyl-alcohol dehydrogenase
1.2.1.16
succinate-semialdehyde dehydrogenase [NAD(P)+]
1.2.1.19
aminobutyraldehyde dehydrogenase
1.2.1.24
succinate-semialdehyde dehydrogenase (NAD+)
1.2.1.28
benzaldehyde dehydrogenase (NAD+)
1.2.1.3
aldehyde dehydrogenase (NAD+)
1.2.1.4
aldehyde dehydrogenase (NADP+)
1.2.1.5
aldehyde dehydrogenase [NAD(P)+]
1.2.1.7
benzaldehyde dehydrogenase (NADP+)
1.2.1.79
succinate-semialdehyde dehydrogenase (NADP+)
|
–
–
–
–
–
–
–
–
–
–
|
| |
BRENDA:
BR29424
KEGG:
R01420
MetaCyc:
BENZALDEHYDE-DEHYDROGENASE-NADP+-RXN
SABIO-RK:
1607
|
|
|
|
4-toluenesulfonate + NADH + O2 <=> sulfite + 4-methylcatechol + NAD+
|
1.14.12
1.14.12.14
2-aminobenzenesulfonate 2,3-dioxygenase
|
–
–
|
| |
KEGG:
R05294
MetaCyc:
TSDOSALCAL-RXN
|
|
|
|
5-methylmaleylacetate + NADH + H+ <=> 2-methyl-3-oxoadipate + NAD+
|
1.3.1.32
maleylacetate reductase
|
–
|
| |
KEGG:
R09224
|
|
|
|
3-methyl-cis,cis-muconate <=> 4-Carboxymethyl-3-methylbut-2-en-1,4-olide
|
5.5.1.1
muconate cycloisomerase
|
–
|
| |
BRENDA:
BS1239
KEGG:
R09229
|
|
|
|
benzaldehyde + H2O + NAD+ <=> aromatic_carboxylate + NADH + H+
|
1.1.1.1
alcohol dehydrogenase
1.2.1.19
aminobutyraldehyde dehydrogenase
1.2.1.24
succinate-semialdehyde dehydrogenase (NAD+)
1.2.1.28
benzaldehyde dehydrogenase (NAD+)
1.2.1.29
aryl-aldehyde dehydrogenase
1.2.1.3
aldehyde dehydrogenase (NAD+)
1.2.1.31
L-aminoadipate-semialdehyde dehydrogenase
1.2.1.48
long-chain-aldehyde dehydrogenase
1.2.1.5
aldehyde dehydrogenase [NAD(P)+]
1.2.1.64
4-hydroxybenzaldehyde dehydrogenase (NAD+)
1.2.1.65
salicylaldehyde dehydrogenase
1.2.1.67
vanillin dehydrogenase
1.2.1.69
fluoroacetaldehyde dehydrogenase
|
–
–
–
–
–
–
–
–
–
–
–
–
–
|
| |
BRENDA:
BR29397;
BR36777
KEGG:
R01419;
R01486
MetaCyc:
ARYL-ALDEHYDE-DEHYDROGENASE-RXN;
BENZALDEHYDE-DEHYDROGENASE-NAD+-RXN
SABIO-RK:
1606
|
|
|
|
H+ + Toluene + O2 + NADH <=> o-Cresol + H2O + NAD+
|
1.14.13.243
toluene 2-monooxygenase
|
–
|
| |
BRENDA:
BR52669
KEGG:
R03560
MetaCyc:
TOLUENE-2-MONOOXYGENASE-RXN
|
|
|
|
3,5-Dichloro-2-methylmuconolactone <=> 3-chloro-2-methyl-dienelactone + Cl- + H+
|
4.5.1
5.5.1.7
chloromuconate cycloisomerase
|
–
–
|
| |
KEGG:
R09217
MetaCyc:
RXN-10101
|
|
|
|
4-formylbenzenesulfonate + NAD+ + H2O <=> H+ + 4-Sulfobenzoate + NADH
|
1.2.1.62
4-formylbenzenesulfonate dehydrogenase
|
–
|
| |
BRENDA:
BR29418
KEGG:
R05272
MetaCyc:
SYDDEHYD-RXN
|
|
|
|
NAD+ + (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol <=> H+ + NADH + 3-methylcatechol
|
1.3.1.19
cis-1,2-dihydrobenzene-1,2-diol dehydrogenase
|
–
|
| |
KEGG:
R04088
MetaCyc:
TOLUENE-DIOL-DEHYDROGENASE-RXN
|
|
|
|
2-methyl-p-cresol + 4 oxidized_azurin + H2O <=> 3-Methyl-4-hydroxybenzaldehyde + 4 azurin + 4 H+
|
1.17.9.1
4-methylphenol dehydrogenase (hydroxylating)
|
–
|
| |
KEGG:
R11194
|
|
|
|
Toluene + O2 + NADPH + H+ <=> m-cresol + NADP+ + H2O
|
1.14.13
|
–
|
| |
KEGG:
R03562
|
|
|
|
p-Cresol + H2O + oxidized_azurin <=> 4-hydroxybenzaldehyde + azurin + H+
|
1.17.9.1
4-methylphenol dehydrogenase (hydroxylating)
|
–
|
| |
BRENDA:
BR40368
KEGG:
R02675
MetaCyc:
1.17.99.1-RXN
|
|
|
|
2-carboxymethyl-3-hydroxyphenylpropionyl-CoA + NAD+ <=> Benzoylsuccinyl-CoA + NADH + H+
|
1.1.1
1.1.1.35
3-hydroxyacyl-CoA dehydrogenase
|
–
–
|
| |
KEGG:
R05575
MetaCyc:
RXN-905
|
|
|
|
m-cresol + O2 + NADH + H+ <=> 3-Hydroxybenzyl_alcohol + NAD+ + H2O
|
1.14.13
|
–
|
| |
KEGG:
R07665
MetaCyc:
3-5-XYLENOL-METHYLHYDROXYLASE-RXN
|
|
|
|
4-Hydroxyisophthalate + O2 + NADPH + H+ <=> 3,4-dihydroxybenzoate + CO2 + NADP+ + H2O
|
1.14.13
|
–
|
| |
KEGG:
R11198
MetaCyc:
RXN-16974
|
|
|
|
4-toluenesulfonate + O2 <=> p-Cresol + sulfate
|
1.14.13
|
–
|
| |
KEGG:
R07663
|
|
|
|
4-carboxymethyl-4-methylbut-2-en-1,4-olide <=> 4-Carboxymethyl-3-methylbut-2-en-1,4-olide
|
5.4.99.14
4-carboxymethyl-4-methylbutenolide mutase
|
–
|
| |
BRENDA:
BR37
KEGG:
R04510
MetaCyc:
5.4.99.14-RXN
|
|
|
|
3-Hydroxybenzaldehyde + NAD+ + H2O <=> 3-hydroxybenzoate + NADH + H+
|
1.2.1.16
succinate-semialdehyde dehydrogenase [NAD(P)+]
1.2.1.24
succinate-semialdehyde dehydrogenase (NAD+)
1.2.1.28
benzaldehyde dehydrogenase (NAD+)
1.2.1.3
aldehyde dehydrogenase (NAD+)
1.2.1.64
4-hydroxybenzaldehyde dehydrogenase (NAD+)
1.2.1.65
salicylaldehyde dehydrogenase
1.2.1.67
vanillin dehydrogenase
1.2.1.7
benzaldehyde dehydrogenase (NADP+)
|
–
–
–
–
–
–
–
–
|
| |
BRENDA:
BS189289
KEGG:
R07667
SABIO-RK:
6943
|
|
|
|
3,5-Dichloro-2-methylmuconolactone <=> H+ + 3,5-Dichloro-2-methylmuconate
|
5.5.1.7
chloromuconate cycloisomerase
|
–
|
| |
KEGG:
R09215
MetaCyc:
RXN-10099
|
|
|
|
2,4-Dichlorotoluene + NADH + O2 + H+ <=> 4,6-Dichloro-3-methyl-cis-1,2-dihydroxycyclohexa-3,5-diene + NAD+
|
1.14.12
|
–
|
| |
KEGG:
R09201
|
|
|
|
Benzoylsuccinyl-CoA + CoA <=> benzoyl-CoA + succinyl-CoA
|
2.3.1
2.3.1.M17
|
–
–
|
| |
KEGG:
R05587
MetaCyc:
RXN-904
|
|
|
|
4-hydroxybenzaldehyde + NAD+ + H2O <=> 4-hydroxybenzoate + NADH + H+
|
1.2.1.28
benzaldehyde dehydrogenase (NAD+)
1.2.1.29
aryl-aldehyde dehydrogenase
1.2.1.3
aldehyde dehydrogenase (NAD+)
1.2.1.64
4-hydroxybenzaldehyde dehydrogenase (NAD+)
1.2.1.65
salicylaldehyde dehydrogenase
1.2.1.67
vanillin dehydrogenase
1.2.1.96
4-hydroxybenzaldehyde dehydrogenase (NADP+)
|
–
–
–
–
–
–
–
|
| |
BRENDA:
BR29420
KEGG:
R01293
MetaCyc:
HYDROXYBENZALDEHYDE-OXIDATION-NAD-RXN;
RXN-13394_WOP
SABIO-RK:
1508
|
|
|
|
4,6-Dichloro-3-methyl-cis-1,2-dihydroxycyclohexa-3,5-diene + NAD+ <=> 4,6-Dichloro-3-methylcatechol + NADH + H+
|
1.3.1
|
–
|
| |
KEGG:
R09213
|
|
|
|
4-Hydroxyisophthalate + O2 + NADH + H+ <=> 3,4-dihydroxybenzoate + H2O + NAD+ + CO2
|
1.14.13
|
–
|
| |
KEGG:
R11197
|
|
|
|
4-carboxymethyl-4-methylbut-2-en-1,4-olide <=> 3-methyl-cis,cis-muconate + H+
|
5.5.1.1
muconate cycloisomerase
5.5.1.7
chloromuconate cycloisomerase
|
–
–
|
| |
BRENDA:
BS368799
KEGG:
R05300
MetaCyc:
RXN-10081
|
|
|
|
benzyl_alcohol + NAD+ <=> benzaldehyde + NADH + H+
|
1.1.1.1
alcohol dehydrogenase
1.1.1.2
alcohol dehydrogenase (NADP+)
1.1.1.21
aldose reductase
1.1.1.245
cyclohexanol dehydrogenase
1.1.1.265
3-methylbutanal reductase
1.1.1.307
D-xylose reductase
1.1.1.347
geraniol dehydrogenase (NAD+)
1.1.1.6
glycerol dehydrogenase
1.1.1.71
alcohol dehydrogenase [NAD(P)+]
1.1.1.73
octanol dehydrogenase
1.1.1.90
aryl-alcohol dehydrogenase
1.14.14.51
(S)-limonene 6-monooxygenase
1.2.1.5
aldehyde dehydrogenase [NAD(P)+]
|
–
–
–
–
–
–
–
–
–
–
–
–
–
|
| |
BRENDA:
BR36722;
BS165076-a
KEGG:
R01487;
R01763
MetaCyc:
ARYL-ALCOHOL-DEHYDROGENASE-RXN;
BENZYL-ALC-DEHYDROGENASE-RXN
SABIO-RK:
1862
|
|
|
|
Toluene + O2 + NADH + H+ <=> (1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol + NAD+
|
1.14.12.11
toluene dioxygenase
|
–
|
| |
BRENDA:
BR40532
KEGG:
R03559
MetaCyc:
TOLUENE-DIOXYGENASE-RXN
|
|
|
|
O2 + NADH + 4-Sulfobenzoate <=> sulfite + NAD+ + 3,4-dihydroxybenzoate
|
1.14.12.8
4-sulfobenzoate 3,4-dioxygenase
|
–
|
| |
BRENDA:
BR40439
KEGG:
R01636
MetaCyc:
4-SULFOBENZOATE-34-DIOXYGENASE-RXN
|
|
|
|
2-Chloro-5-methyl-cis-dienelactone + H2O <=> 2-chloro-5-methylmaleylacetate + H+
|
3.1.1
3.1.1.45
carboxymethylenebutenolidase
|
–
–
|
| |
KEGG:
R09222
MetaCyc:
RXN-10106
|
|
|
|
2-carboxymethyl-3-hydroxyphenylpropionyl-CoA <=> (E)-2-benzylidenesuccinyl-CoA + H2O
|
4.2.1
|
–
|
| |
KEGG:
R05599
MetaCyc:
RXN-902
|
|
|
|
4-methylcatechol + O2 <=> 3-methyl-cis,cis-muconate + H+
|
1.13.11.1
catechol 1,2-dioxygenase
1.13.11.3
protocatechuate 3,4-dioxygenase
|
–
–
|
| |
BRENDA:
BS260576
KEGG:
R05299
MetaCyc:
RXN-10080
SABIO-RK:
4908
|
|
|
|
4-methyl-3-oxoadipate_enol-lactone + H2O <=> 4-methyl-3-oxoadipate + H+
|
3.1.1
3.1.1.24
3-oxoadipate enol-lactonase
|
–
–
|
| |
BRENDA:
BS416319
KEGG:
R09226
MetaCyc:
RXN-10083
|
|
|
|
(R)-2-benzylsuccinate <=> Toluene + fumarate
|
4.1.99.11
benzylsuccinate synthase
|
–
|
| |
BRENDA:
BR22822
KEGG:
R05598
MetaCyc:
RXN-863
|
|
|
|
3,5-Dichloro-2-methylmuconate <=> 2-Chloro-5-methyl-cis-dienelactone + Hydrochloric_acid
|
5.5.1.7
chloromuconate cycloisomerase
|
–
|
| |
KEGG:
R09221
|
|
|
|
3-Hydroxybenzaldehyde + NADP+ + H2O <=> 3-hydroxybenzoate + NADPH + H+
|
1.2.1.5
aldehyde dehydrogenase [NAD(P)+]
1.2.1.7
benzaldehyde dehydrogenase (NADP+)
|
–
–
|
| |
BRENDA:
BS231674
KEGG:
R07666
MetaCyc:
3-OH-BENZALDEHYDE-DEHYDROG-NADP+-RXN
|
|
|
|
3-Hydroxybenzyl_alcohol + NADP+ <=> 3-Hydroxybenzaldehyde + NADPH + H+
|
1.1.1.184
carbonyl reductase (NADPH)
1.1.1.91
aryl-alcohol dehydrogenase (NADP+)
1.1.1.97
3-hydroxybenzyl-alcohol dehydrogenase
|
–
–
–
|
| |
BRENDA:
BR29353
KEGG:
R04136
MetaCyc:
1.1.1.97-RXN
SABIO-RK:
3857
|
|
|
|
2-chloro-5-methylmaleylacetate + NADH + H+ <=> 5-methylmaleylacetate + NAD+ + Hydrochloric_acid
|
1.3.1.32
maleylacetate reductase
|
–
|
| |
KEGG:
R09223
|
|
|
|
3-Methyl-4-hydroxybenzaldehyde + NADP+ + H2O <=> 4-hydroxy-3-methylbenzoate + NADPH + H+
|
1.2.1.96
4-hydroxybenzaldehyde dehydrogenase (NADP+)
|
–
|
| |
BRENDA:
BS433281
KEGG:
R11195
MetaCyc:
RXN-16970
SABIO-RK:
15065
|
|
|
|
m-cresol + NADPH + H+ + O2 <=> 3-methylcatechol + NADP+ + H2O
|
1.14.13.7
phenol 2-monooxygenase (NADPH)
|
–
|
| |
BRENDA:
BS440785
KEGG:
R03566
|
|
|
|
H+ + o-Cresol + NADH + O2 <=> 3-methylcatechol + NAD+ + H2O
|
1.14.13.236
toluene 4-monooxygenase
1.14.13.243
toluene 2-monooxygenase
1.14.13.44
2-hydroxybiphenyl 3-monooxygenase
1.14.13.7
phenol 2-monooxygenase (NADPH)
|
–
–
–
–
|
| |
BRENDA:
BR52670
KEGG:
R03608
MetaCyc:
O-CRESOL-METHYLCATECHOL-RXN
|
|
|
|
4-hydroxybenzaldehyde + NADP+ + H2O <=> 4-hydroxybenzoate + NADPH + H+
|
1.2.1.4
aldehyde dehydrogenase (NADP+)
1.2.1.5
aldehyde dehydrogenase [NAD(P)+]
1.2.1.67
vanillin dehydrogenase
1.2.1.7
benzaldehyde dehydrogenase (NADP+)
1.2.1.96
4-hydroxybenzaldehyde dehydrogenase (NADP+)
|
–
–
–
–
–
|
| |
BRENDA:
BR51337
KEGG:
R01294
MetaCyc:
HYDROXYBENZALDEHYDE-OXIDATION-NADP-RXN;
RXN-13394
SABIO-RK:
1509
|
|
|
|
4-(hydroxymethyl)benzenesulfonate + NAD+ <=> 4-formylbenzenesulfonate + H+ + NADH
|
1.1.1.257
4-(hydroxymethyl)benzenesulfonate dehydrogenase
|
–
|
| |
BRENDA:
BR22609
KEGG:
R05271
MetaCyc:
SOLDEHYD-RXN
|
|
|
|
4-Carboxymethyl-3-methylbut-2-en-1,4-olide <=> 4-methyl-3-oxoadipate_enol-lactone
|
5.3.3
5.3.3.4
muconolactone Delta-isomerase
5.4.99.14
4-carboxymethyl-4-methylbutenolide mutase
5.5.1
|
–
–
–
–
|
| |
BRENDA:
BS407053
KEGG:
R09225
MetaCyc:
RXN-10082
|
|
|
|
4-hydroxy-3-methylbenzoate <=> 4-Hydroxyisophthalate
|
not assigned
|
–
|
| |
KEGG:
R11196
|
|
|
|
H+ + 4-toluenesulfonate + O2 + NADH <=> 4-(hydroxymethyl)benzenesulfonate + NAD+ + H2O
|
1.14.13
1.14.99
|
–
–
|
| |
KEGG:
R05281
MetaCyc:
TSMOS-RXN
|
|
|
|
3-chloro-2-methyl-dienelactone + H2O <=> 3-chloro-2-methylmaleylacetate + H+
|
3.1.1.45
carboxymethylenebutenolidase
|
–
|
| |
BRENDA:
BS364270;
BS364271
KEGG:
R09220
MetaCyc:
RXN-10107
|
|
|
|
succinyl-CoA + (R)-2-benzylsuccinate <=> succinate + (R)-2-benzylsuccinyl-CoA
|
2.8.3.15
succinyl-CoA:(R)-benzylsuccinate CoA-transferase
|
–
|
| |
BRENDA:
BR47454
KEGG:
R05588
MetaCyc:
RXN-864
SABIO-RK:
15391
|
|
|
|
4,6-Dichloro-3-methylcatechol + O2 <=> 3,5-Dichloro-2-methylmuconate + H+
|
1.13.11
|
–
|
| |
KEGG:
R09214
MetaCyc:
RXN-10096
|
|
|
|
Toluene + O2 + NADH + H+ <=> p-Cresol + H2O + NAD+
|
1.14.13.236
toluene 4-monooxygenase
|
–
|
| |
BRENDA:
BR52031
KEGG:
R05666
MetaCyc:
TOLUENE-4-MONOOXYGENASE-RXN
|
|
|
|
(R)-2-benzylsuccinyl-CoA + flavin <=> (E)-2-benzylidenesuccinyl-CoA + reduced_flavodoxin
|
1.3.8.3
(R)-benzylsuccinyl-CoA dehydrogenase
|
–
|
| |
BRENDA:
BR47377
KEGG:
R05584
|
|
