|
|
ATP + perillic_acid + CoA <=> Perillyl-CoA + AMP + diphosphate
|
6.2.1
6.2.1.M31
|
–
–
|
|
KEGG:
R06368
MetaCyc:
RXN-20141
|
|
|
|
(1R,2R,4S)-limonene-1,2-diol + NAD+ <=> (1R,4S)-1-hydroxy-2-oxolimonene + NADH + H+
|
1.1.1.297
limonene-1,2-diol dehydrogenase
|
–
|
|
BRENDA:
BR48901
KEGG:
R09388
MetaCyc:
RXN-9948
|
|
|
|
2-Hydroxy-4-isopropenylcyclohexane-1-carboxyl-CoA + acceptor <=> 4-Isopropenyl-2-oxy-cyclohexanecarboxyl-CoA + reduced_acceptor
|
1.1
|
–
|
|
KEGG:
R06370
|
|
|
|
(3S,6S)-6-Isopropenyl-3-methyl-2-oxo-oxepanone + H2O <=> (5S)-6-Hydroxy-5-isopropenyl-2-methylhexanoate + H+
|
3.1.1.83
monoterpene epsilon-lactone hydrolase
|
–
|
|
KEGG:
R06393
MetaCyc:
RXN-9432
|
|
|
|
(1R,2R,4R)-dihydrocarveol + NAD+ <=> (4R)-dihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
BRENDA:
BS395039
KEGG:
R06376
MetaCyc:
RXN-9424
|
|
|
|
6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-methanol + O2 + acceptor <=> myrtenal + 2 H2O + reduced_acceptor
|
1.1
|
–
|
|
KEGG:
R06402
|
|
|
|
(1S,2S,4R)-iso-dihydrocarveol + NAD+ <=> (1R,4S)-isodihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
KEGG:
R06377
MetaCyc:
RXN-9426
|
|
|
|
(3R)-6-Hydroxy-3-isopropenyl-heptanoate <=> (3R)-3-isopropenyl-6-oxoheptanoate
|
not assigned
|
–
|
|
KEGG:
R06394
|
|
|
|
(-)-limonene + NADPH + H+ + O2 <=> (4S)-limonene-1,2-epoxide + NADP+ + H2O
|
1.14.13.107
limonene 1,2-monooxygenase
|
–
|
|
KEGG:
R09389
MetaCyc:
RXN-9409
|
|
|
|
(4S)-7-Hydroxy-4-isopropenyl-7-methyl-2-oxo-oxepanone <=> H+ + (3S)-3-isopropenyl-6-oxoheptanoate
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R09391
MetaCyc:
RXN-9418
|
|
|
|
3-Hydroxy-2,6-dimethyl-5-methylene-heptanoyl-CoA + NAD+ <=> 2,6-Dimethyl-5-methylene-3-oxo-heptanoyl-CoA + NADH + H+
|
1.1
|
–
|
|
KEGG:
R06413
|
|
|
|
cis-2-Methyl-5-isopropylhexa-2,5-dienoic_acid + ATP + CoA <=> cis-2-Methyl-5-isopropylhexa-2,5-dienoyl-CoA + AMP + diphosphate
|
6.2.1
|
–
|
|
KEGG:
R06409
|
|
|
|
(4R)-dihydrocarvone + NADPH + H+ + O2 <=> (4R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
BRENDA:
BS395043
KEGG:
R06386
MetaCyc:
RXN-9391
SABIO-RK:
12383
|
|
|
|
(3S,6R)-6-Isopropenyl-3-methyl-2-oxo-oxepanone + H2O <=> (5R)-6-Hydroxy-5-isopropenyl-2-methylhexanoate + H+
|
3.1.1.83
monoterpene epsilon-lactone hydrolase
|
–
|
|
KEGG:
R06391
MetaCyc:
RXN-9436
|
|
|
|
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2 <=> (4S)-7-Hydroxy-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R09390
MetaCyc:
RXN-9416
|
|
|
|
trans-2-Methyl-5-isopropylhexa-2,5-dienoyl-CoA + H2O <=> 3-Hydroxy-2,6-dimethyl-5-methylene-heptanoyl-CoA
|
4.2.1.17
enoyl-CoA hydratase
|
–
|
|
KEGG:
R06412
|
|
|
|
Perillyl-CoA + H2O <=> 2-Hydroxy-4-isopropenylcyclohexane-1-carboxyl-CoA
|
4.2.1
|
–
|
|
KEGG:
R06369
MetaCyc:
RXN-20142
|
|
|
|
(4R)-7-Hydroxy-4-isopropenyl-7-methyl-2-oxo-oxepanone <=> H+ + (3R)-3-isopropenyl-6-oxoheptanoate
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R09392
MetaCyc:
RXN-9417
|
|
|
|
(4R)-dihydrocarvone + acceptor <=> (-)-Carvone + reduced_acceptor
|
1.3.99.25
carvone reductase
|
–
|
|
BRENDA:
BR48902
KEGG:
R06373
MetaCyc:
RXN-9403
|
|
|
|
1,2-epoxymenth-8-ene + H2O <=> (1S,2S,4R)-limonene-1,2-diol
|
3.3.2.8
limonene-1,2-epoxide hydrolase
|
–
|
|
BRENDA:
BS380045
KEGG:
R05784
MetaCyc:
3.3.2.8-RXN;
RXN-9412
|
|
|
|
2,6-Dimethyl-5-methylene-3-oxo-heptanoyl-CoA + CoA <=> 3-isopropylbut-3-enoyl-CoA + propionyl-CoA
|
2.3.1
|
–
|
|
KEGG:
R06414
|
|
|
|
myrtenal + H2O + acceptor <=> Myrtenic_acid + reduced_acceptor
|
1.2
|
–
|
|
KEGG:
R06403
|
|
|
|
(-)-alpha-pinene + O2 + 2 H+ + 2 e- <=> pino-carveol + H2O
|
1.14
|
–
|
|
KEGG:
R06404
|
|
|
|
3-isopropylbut-3-enoyl-CoA + H2O <=> 3-Isopropyl-3-butenoic_acid + CoA
|
3.1.2
|
–
|
|
KEGG:
R06415
|
|
|
|
(1S,2R,4R)-neoisodihydrocarveol + NAD+ <=> (-)-dihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
KEGG:
R06385
MetaCyc:
RXN-9430
|
|
|
|
(-)-limonene + NADH + H+ + O2 <=> (4S)-limonene-1,2-epoxide + NAD+ + H2O
|
1.14.13.107
limonene 1,2-monooxygenase
|
–
|
|
KEGG:
R09385
MetaCyc:
RXN-9409_WOP
|
|
|
|
(+)-limonene + NADH + H+ + O2 <=> (R)-1,2-epoxy-limonene + NAD+ + H2O
|
1.14.13.107
limonene 1,2-monooxygenase
|
–
|
|
BRENDA:
BR49012-a
KEGG:
R06398
MetaCyc:
RXN-9407_WOP
|
|
|
|
(-)-alpha-pinene + NADH + H+ + O2 <=> alpha-Pinene_oxide + NAD+ + H2O
|
1.14.13
1.14.13.155
alpha-pinene monooxygenase
|
–
–
|
|
BRENDA:
BR50101
KEGG:
R06406
MetaCyc:
RXN-12972
|
|
|
|
(1R,4S)-isodihydrocarvone + NADPH + H+ + O2 <=> 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R06387
MetaCyc:
RXN-9420
|
|
|
|
(+)-trans-carveol + NAD+ <=> (S)-carvone + NADH + H+
|
1.1.1.275
(+)-trans-carveol dehydrogenase
|
–
|
|
BRENDA:
BR47616
KEGG:
R06117
MetaCyc:
RXN-9397
|
|
|
|
(+)-limonene + reduced_flavodoxin + O2 <=> (+)-trans-carveol + flavin + H2O
|
1.14.14.53
(R)-limonene 6-monooxygenase
|
–
|
|
BRENDA:
BR47606
KEGG:
R06119
|
|
|
|
(1R,4S)-isodihydrocarvone + O2 + NADPH + H+ <=> (3S,6R)-6-Isopropenyl-3-methyl-2-oxo-oxepanone + H2O + NADP+
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R06388
MetaCyc:
RXN-9435
|
|
|
|
(-)-alpha-pinene + reduced_acceptor + O2 <=> 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-methanol + H2O + acceptor
|
1.14
|
–
|
|
KEGG:
R06401
|
|
|
|
4-isopropenyl-7-methyloxepan-2-one + H2O <=> 6-hydroxy-3-isopropenylheptanoate + H+
|
3.1.1.83
monoterpene epsilon-lactone hydrolase
|
–
|
|
BRENDA:
BR48911
KEGG:
R06392
MetaCyc:
RXN-9393
|
|
|
|
(4S)-limonene-1,2-epoxide + H2O <=> (1R,2R,4S)-limonene-1,2-diol
|
3.3.2.8
limonene-1,2-epoxide hydrolase
|
–
|
|
KEGG:
R09387
MetaCyc:
RXN-9413
|
|
|
|
6-hydroxy-3-isopropenylheptanoate <=> (3S)-3-isopropenyl-6-oxoheptanoate
|
not assigned
|
–
|
|
KEGG:
R06395
|
|
|
|
(-)-trans-carveol + NADP+ <=> (-)-Carvone + NADPH + H+
|
1.1.1.243
carveol dehydrogenase
1.3.1.102
2-alkenal reductase (NADP+)
|
–
–
|
|
BRENDA:
BR29279
KEGG:
R03114
MetaCyc:
CARVEOL-DEHYDROGENASE-RXN
SABIO-RK:
2951
|
|
|
|
(1R,4S)-isodihydrocarvone <=> (-)-dihydrocarvone
|
not assigned
|
–
|
|
KEGG:
R06381
MetaCyc:
RXN-9428
|
|
|
|
perillyl_alcohol + NAD+ <=> perillaldehyde + NADH + H+
|
1.1.1.1
alcohol dehydrogenase
1.1.1.144
perillyl-alcohol dehydrogenase
1.1.1.347
geraniol dehydrogenase (NAD+)
1.1.1.90
aryl-alcohol dehydrogenase
1.14.14.51
(S)-limonene 6-monooxygenase
|
–
–
–
–
–
|
|
BRENDA:
BR29210;
BS257291;
BS425213
KEGG:
R03945
MetaCyc:
PERILLYL-ALCOHOL-DEHYDROGENASE-RXN;
RXN-20140
|
|
|
|
4-Isopropenyl-2-oxy-cyclohexanecarboxyl-CoA + H2O <=> 3-Isopropenylpimelyl-CoA
|
3.7.1
|
–
|
|
KEGG:
R06371
|
|
|
|
(4R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + H2O <=> (3R)-6-Hydroxy-3-isopropenyl-heptanoate
|
3.1.1.83
monoterpene epsilon-lactone hydrolase
|
–
|
|
KEGG:
R06390
|
|
|
|
cis-2-Methyl-5-isopropylhexa-2,5-dienoyl-CoA + H2O <=> 3-Hydroxy-2,6-dimethyl-5-methylene-heptanoyl-CoA
|
4.2.1.17
enoyl-CoA hydratase
|
–
|
|
KEGG:
R06411
|
|
|
|
(1R,4S)-isodihydrocarvone + acceptor <=> (S)-carvone + reduced_acceptor
|
1.3.99.25
carvone reductase
|
–
|
|
BRENDA:
BR48903
KEGG:
R06372
MetaCyc:
RXN-9419
|
|
|
|
(+)-limonene + NADPH + H+ + O2 <=> (R)-1,2-epoxy-limonene + NADP+ + H2O
|
1.14.13.107
limonene 1,2-monooxygenase
|
–
|
|
BRENDA:
BR49012
KEGG:
R09393
MetaCyc:
RXN-9407
|
|
|
|
(1R,2S,4R)-neo-dihydrocarveol + NAD+ <=> (4R)-dihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
BRENDA:
BS395042
KEGG:
R06378
MetaCyc:
RXN-9392
|
|
|
|
(3S)-3-isopropenyl-6-oxoheptanoate <=> (3S)-3-Isopropenyl-6-oxoheptanoyl-CoA
|
6.2.1
|
–
|
|
KEGG:
R06397
|
|
|
|
(4R)-dihydrocarvone <=> (1R,4S)-isodihydrocarvone
|
not assigned
|
–
|
|
KEGG:
R06380
MetaCyc:
RXN-9427
|
|
|
|
(1S,2S,4R)-iso-dihydrocarveol + NAD+ <=> (1R,4S)-isodihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
BRENDA:
BS395050
KEGG:
R06382
MetaCyc:
RXN-9433
|
|
|
|
(+)-dihydrocarveol + NAD+ <=> (-)-dihydrocarvone + NADH + H+
|
1.1.1.198
(+)-borneol dehydrogenase
1.1.1.296
dihydrocarveol dehydrogenase
|
–
–
|
|
BRENDA:
BS187487
KEGG:
R06383
MetaCyc:
RXN-9429
|
|
|
|
perillic_acid + CoA + ATP <=> Perillyl-CoA + H2O + ADP + phosphate
|
6.2.1
|
–
|
|
KEGG:
R06367
|
|
|
|
trans-2-Methyl-5-isopropylhexa-2,5-dienoic_acid + ATP + CoA <=> trans-2-Methyl-5-isopropylhexa-2,5-dienoyl-CoA + AMP + diphosphate
|
6.2.1
|
–
|
|
KEGG:
R06410
|
|
|
|
alpha-Pinene_oxide <=> (Z)-2-Methyl-5-isopropylhexa-2,5-dienal
|
5.5.1.10
alpha-pinene-oxide decyclase
|
–
|
|
BRENDA:
BR48378
KEGG:
R04040
MetaCyc:
ALPHA-PINENE-OXIDE-DECYCLASE-RXN
|
|
|
|
(-)-dihydrocarvone + O2 + NADPH + H+ <=> (3S,6S)-6-Isopropenyl-3-methyl-2-oxo-oxepanone + H2O + NADP+
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R06389
MetaCyc:
RXN-9431
|
|
|
|
(1S,2S,4R)-limonene-1,2-diol + NAD+ <=> (1S,4R)-1-hydroxy-2-oxolimonene + NADH + H+
|
1.1.1.297
limonene-1,2-diol dehydrogenase
|
–
|
|
BRENDA:
BR48900
KEGG:
R06399
MetaCyc:
RXN-9949
|
|
|
|
(-)-limonene + reduced_flavodoxin + O2 <=> (S)-perillyl_alcohol + flavin + H2O
|
1.14.14.52
(S)-limonene 7-monooxygenase
|
–
|
|
BRENDA:
BR36765
KEGG:
R02470
|
|
|
|
trans-2-Methyl-5-isopropylhexa-2,5-dienal + NAD+ + H2O <=> trans-2-Methyl-5-isopropylhexa-2,5-dienoic_acid + NADH + H+
|
1.2.1
|
–
|
|
KEGG:
R06408
|
|
|
|
(1R,2S,4R)-neo-dihydrocarveol + NAD+ <=> (1R,4S)-isodihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
KEGG:
R06379
MetaCyc:
RXN-9425
|
|
|
|
(1S,2R,4R)-neoisodihydrocarveol + NAD+ <=> (1R,4S)-isodihydrocarvone + NADH + H+
|
1.1.1.296
dihydrocarveol dehydrogenase
|
–
|
|
BRENDA:
BS395049
KEGG:
R06384
MetaCyc:
RXN-9434
|
|
|
|
(-)-cis-carveol <=> (-)-Carvone
|
not assigned
|
–
|
|
KEGG:
R06374
|
|
|
|
(3R)-3-isopropenyl-6-oxoheptanoate + CoA + ATP <=> (3R)-3-Isopropenyl-6-oxoheptanoyl-CoA + H2O + AMP + diphosphate
|
6.2.1
|
–
|
|
KEGG:
R06515
|
|
|
|
(-)-limonene + reduced_flavodoxin + O2 <=> (-)-trans-carveol + flavin + H2O
|
1.14.14.51
(S)-limonene 6-monooxygenase
|
–
|
|
BRENDA:
BR36764
KEGG:
R02468
|
|
|
|
perillaldehyde + NAD+ + H2O <=> perillic_acid + NADH + H+
|
1.2.1.28
benzaldehyde dehydrogenase (NAD+)
1.2.1.3
aldehyde dehydrogenase (NAD+)
|
–
–
|
|
BRENDA:
BS258079
KEGG:
R06366
MetaCyc:
RXN-14280
|
|
|
|
(2S,4S)-carveol <=> (S)-carvone
|
not assigned
|
–
|
|
KEGG:
R06375
|
|
|
|
(3R)-3-isopropenyl-6-oxoheptanoate + CoA + ATP <=> (3R)-3-Isopropenyl-6-oxoheptanoyl-CoA + ADP + phosphate
|
6.2.1
|
–
|
|
KEGG:
R06396
MetaCyc:
RXN-9406
|
|
|
|
(Z)-2-Methyl-5-isopropylhexa-2,5-dienal + NAD+ + H2O <=> cis-2-Methyl-5-isopropylhexa-2,5-dienoic_acid + NADH + H+
|
1.2.1
|
–
|
|
KEGG:
R06407
|
|
|
|
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2 <=> (4R)-7-Hydroxy-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
|
1.14.13.105
monocyclic monoterpene ketone monooxygenase
|
–
|
|
KEGG:
R06400
MetaCyc:
RXN-9415
|
|
|
|
pino-carveol <=> (-)-pinocarvone + H+
|
1.1
|
–
|
|
KEGG:
R06405
|
|