PW000981
PathWhiz
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=CC(=C1)C(O)=O
17215925
ChemSpider
C48H74
2-Octaprenyl-6-hydroxyphenol
650.57904
CPD-9956
BioCyc
937
ChemSpider
P0AGK1
UniProt
HMDB0012199
HMDB
BiologicalState304
Bacteria
1.0
P25535
UniProt
132
ChemSpider
P25534
UniProt
SMILES
O
HMDB0001060
HMDB
Pyrophosphate
C46H70O
2-Octaprenylphenol
638.54266
HMDB0001185
HMDB
1.0
C49H76O4
Ubiquinol-8
728.57434
C00448
KEGG Compound
Reduced acceptor
P0AD57
UniProt
Chorismate Biosynthesis
SubPathway
Chorismate--pyruvate lyase
1.0
393270
ChemSpider
1.0
Pyruvic acid
559142
ChemSpider
CHEBI:60655
ChEBI
C3H4O3
Pyruvic acid
88.016045
CHEBI:1617
ChEBI
C15H23N6O5S
S-Adenosylmethionine
399.14505
53-59-8
CAS
2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase
1038
PubChem-compound
4444251
ChemSpider
Ubiquinol-8
SubPathwayInput
CHEBI:16474
ChEBI
CHEBI:15022
ChEBI
952
ChemSpider
SMILES
O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
GO:0005829
GENE ONTOLOGY
274
ChemSpider
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid Biosynthesis
SubPathway
2.5.1.90
false
2.5.1.90
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate → Octaprenyl diphosphate + 5 Pyrophosphate
LEFT_TO_RIGHT
PW000958
PathWhiz
135
PubChem-compound
2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol
ADENOSYL-HOMO-CYS
BioCyc
Pyrophosphate
485-80-3
CAS
NADPH
C04146
KEGG Compound
octaprenyl diphosphate synthase
CHEBI:17333
ChEBI
3-demethylubiquinol-8
445713
PubChem-compound
1010
ChemSpider
4-Hydroxybenzoic acid
CHEBI:30763
ChEBI
1.0
NADP
PPI
BioCyc
Octaprenyl diphosphate
HMDB0001094
HMDB
C21H30N7O17P3
NADPH
745.0911
C21H29N7O17P3
NADP
744.08325
C7H6O3
4-Hydroxybenzoic acid
138.0317
1.0
NADPH
BioCyc
Hydrogen Ion
SMILES
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
979-92-0
CAS
C5H12O7P2
Isopentenyl pyrophosphate
246.00583
3-demethylubiquinone-9 3-methyltransferase
Cytosol
CPD-6641
BioCyc
C14H20N6O5S
S-Adenosylhomocysteine
384.12158
Ubiquinone/menaquinone biosynthesis methyltransferase ubiE
2-octaprenyl-6-methoxyphenol hydroxylase
54685638
PubChem-compound
P0A887
UniProt
HMDB0000217
HMDB
Oxygen
124-38-9
CAS
C00129
KEGG Compound
1158
ChemSpider
C00007
KEGG Compound
C00006
KEGG Compound
CHEBI:15414
ChEBI
CHEBI:18009
ChEBI
oxidized electron acceptor
SMP0000974
SMPDB
C00001
KEGG Compound
CHEBI:18361
ChEBI
C00005
KEGG Compound
Farnesyl pyrophosphate
SubPathwayOutput
1031
ChemSpider
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
SMILES
OC(=O)C1=CC=C(O)C=C1
3-octaprenyl-4-hydroxybenzoate carboxy-lyase
1.0
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
CHEBI:61705
ChEBI
53-57-6
CAS
C00019
KEGG Compound
74075-00-6
CAS
C00011
KEGG Compound
SMILES
O=C=O
S-ADENOSYLMETHIONINE
BioCyc
C00251
KEGG Compound
CHEBI:16275
ChEBI
C00013
KEGG Compound
O7P2
Pyrophosphate
173.91193
NAD(P)
BioCyc
P26602
UniProt
2-Octaprenylphenol
Octaprenyl-diphosphate synthase
562
TAXONOMY
H
Hydrogen Ion
1.007825
2-Octaprenyl-6-hydroxyphenol
388301
ChemSpider
S-Adenosylhomocysteine
2-octaprenylphenol hydroxylase
SMP0000997
SMPDB
2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase
Oxidative Phosphorylation
SubPathway
C00022
KEGG Compound
C00021
KEGG Compound
SMILES
COC1=C(O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C\C=C(/C)CC=C(C)C)=C(C)C(O)=C1
HMDB0000243
HMDB
Octaprenyl diphosphate
1.0
C40H68O7P2
Octaprenyl diphosphate
722.44403
SMILES
COC1=CC=CC(C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)CC=C(C)C)=C1O
1.0
1.0
2.1.1.222
false
2.1.1.222
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine → 2-methoxy-6-(all-trans-octaprenyl)phenol + Hydrogen Ion + S-Adenosylhomocysteine
LEFT_TO_RIGHT
1.14.13.-
false
1.14.13.-
2-Octaprenylphenol + Hydrogen Ion + NADPH + Oxygen → 2-Octaprenyl-6-hydroxyphenol + NADP + Water
LEFT_TO_RIGHT
4.1.1.-
false
4.1.1.-
3-Octaprenyl-4-hydroxybenzoate + Hydrogen Ion → 2-Octaprenylphenol + Carbon dioxide
LEFT_TO_RIGHT
24603698
ChemSpider
2.5.1.-
false
2.5.1.-
4-Hydroxybenzoic acid + Octaprenyl diphosphate → 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate
LEFT_TO_RIGHT
CHEBI:40407
ChEBI
372-97-4
CAS
5.0
C00156
KEGG Compound
1.0
2-octaprenyl-6-methoxyphenol hydroxylase
Water
1.0
HMDB0001347
HMDB
1.0
4.1.3.40
false
4.1.3.40
Chorismate → 4-Hydroxybenzoic acid + Pyruvic acid
LEFT_TO_RIGHT
4-hydroxybenzoate octaprenyltransferase
HMDB0000250
HMDB
SMILES
[O-]P([O-])(=O)OP([O-])([O-])=O
14000-31-8
CAS
SMP0000936
SMPDB
3-Octaprenyl-4-hydroxybenzoate
2-methoxy-6-(all-trans-octaprenyl)phenol
C46H70O3
6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
670.5325
C10H10O6
Chorismate
226.04774
5675
ChemSpider
HMDB0000939
HMDB
P17993
UniProt
1.0
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
11542
ChemSpider
C40H58O2
2-methoxy-6-(all-trans-octaprenyl)phenol
570.44366
SubPathwayInteraction109904
SubPathway109904Reaction
SubPathwayReaction
SMILES
[H]OC1=C([H])C(=C(O[H])C(OC([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]
SubPathwayInteraction109903
SubPathway109903Reaction
SubPathwayReaction
SMILES
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)=C(OC)C(O)=C1O)=C(\C)CCC=C(C)C
C15H28O7P2
Farnesyl pyrophosphate
382.13104
SubPathwayInteraction109905
SubPathwayReaction
SubPathway109905Reaction
C47H70O3
3-Octaprenyl-4-hydroxybenzoate
682.5325
Escherichia coli
1.0
7732-18-5
CAS
2.0
Reduced acceptor
1.0
Chorismate
SubPathwayOutput
3-octaprenyl-4-hydroxybenzoate carboxy-lyase
3-octaprenyl-4-hydroxybenzoate carboxy-lyase
617-12-9
CAS
O2
Oxygen
31.98983
127-17-3
CAS
1.0
22833558
PubChem-compound
Isopentenyl pyrophosphate
bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase
1.0
SMP0000836
SMPDB
99-96-7
CAS
CHEBI:16526
ChEBI
FARNESYL-PP
BioCyc
SMILES
COC1=C(OC)C(O)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(C)=C1O
7782-44-7
CAS
HMDB0001377
HMDB
P75728
UniProt
SMILES
CC(=O)C(O)=O
HMDB0000961
HMDB
5280651
PubChem-compound
1.0
CHEBI:1233
ChEBI
Octaprenyl-diphosphate synthase
CHEBI:1235
ChEBI
Reaction3723
false
3-demethylubiquinol-8 + S-Adenosylmethionine → Hydrogen Ion + S-Adenosylhomocysteine + Ubiquinol-8
LEFT_TO_RIGHT
1.14.13.-
false
1.14.13.-
6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + Oxygen + Reduced acceptor → 3-demethylubiquinol-8 + Water + oxidized electron acceptor
LEFT_TO_RIGHT
2.1.1.163
false
2.1.1.163
2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + S-Adenosylmethionine → 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + Hydrogen Ion + S-Adenosylhomocysteine
LEFT_TO_RIGHT
1.14.13.-
false
1.14.13.-
2-methoxy-6-(all-trans-octaprenyl)phenol + Hydrogen Ion + NADPH + Oxygen → 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + NADP + Water
LEFT_TO_RIGHT
962
PubChem-compound
CPD-9517
BioCyc
31983
ChemSpider
1.0
358-71-4
CAS
C48H74O4
3-demethylubiquinol-8
714.5587
6.0
C47H72O3
2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol
684.54816
5.0
CO2
Carbon dioxide
43.98983
SMILES
[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
P0AAB4
UniProt
4-hydroxybenzoate octaprenyltransferase
C00080
KEGG Compound
2.0
SMILES
O=O
Chorismate--pyruvate lyase
Secondary Metabolites: Ubiquinol Biosynthesis
CHEBI:32816
ChEBI
HMDB0002111
HMDB
PW000816
PathWhiz
CHEBI:15377
ChEBI
1.0
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
PYRUVATE
BioCyc
5886
PubChem-compound
S-Adenosylmethionine
CHEBI:16584
ChEBI
5280832
PubChem-compound
1.0
HMDB0000500
HMDB
280
PubChem-compound
ReactionCatalysis3676
ACTIVATION
5280833
PubChem-compound
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(C)C(C)=CC=C1
CHEBI:61682
ChEBI
2
TAXONOMY
644102
PubChem-compound
1195
PubChem-compound
CHEBI:17407
ChEBI
2-octaprenylphenol hydroxylase
SMILES
CC(=C)CCOP(O)(=O)OP(O)(O)=O
SMILES
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
22833512
PubChem-compound
25246222
PubChem-compound
PW000919
PathWhiz
ReactionCatalysis3688
ACTIVATION
ReactionCatalysis3689
ACTIVATION
1.0
H2O
Water
18.010565
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC=CC=C1O
1060
PubChem-compound
Farnesyl pyrophosphate
1.0
977
PubChem-compound
ReactionCatalysis3690
ACTIVATION
HMDB0059597
HMDB
oxidized electron acceptor
Carbon dioxide
HMDB0001967
HMDB
CHEBI:16680
ChEBI
12039
PubChem-compound
24762165
PubChem-compound
Ubiquinone/menaquinone biosynthesis methyltransferase ubiE
3-demethylubiquinone-9 3-methyltransferase
1.0
ReactionCatalysis3693
ACTIVATION
ReactionCatalysis3694
ACTIVATION
OCTAPRENYL-DIPHOSPHATE
BioCyc
ReactionCatalysis3691
ACTIVATION
ReactionCatalysis3692
ACTIVATION
ReactionCatalysis3695
ACTIVATION
ReactionCatalysis3696
ACTIVATION