superpathway of menaquinol-8 biosynthesis I
MetaCyc:PWY-5838
The complete E. coli K-12 classical menaquinol-8 superpathway contains ten reactions: seven steps convert chorismate to 1,4-dihydroxy-2-naphthoate, IspB extends farnesyl diphosphate with five isopentenyl diphosphates, and MenA and UbiE prenylate and methylate the naphthalenediol to menaquinol-8. This is the full native PWY-5838 boundary, including its octaprenyl donor branch; upstream chorismate, IPP and farnesyl diphosphate synthesis and downstream respiratory redox cycling are separate. MenF is the dedicated isochorismate synthase. MenD forms SEPHCHC, MenH releases pyruvate, and MenI hydrolyzes DHNA-CoA; older assignments that collapsed these activities are superseded. K-12 protein annotation and MG1655 native frames are distinguished from primary experiments in specific K-12 derivatives, including XL1 Blue and BW25113. The quinol endpoint follows exact native reactions and current Rhea chemistry; older quinone extraction studies do not directly establish intracellular redox occupancy. Native MenE tetramer, reviewed homodimer by similarity and monomeric inhibitor-bound crystal assemblies disagree, so its edge expresses supported function without resolving assembly. MenC, MenA and UbiE functional edges likewise do not assert isolated-monomer sufficiency. UbiE membership in the ubiquinone metabolon is not transferred to this pathway. Magnesium and manganese alternatives for MenD and inferred IspB magnesium binding retain their evidence limits; bicarbonate is a supported MenB cofactor, not a stoichiometric substrate.
- Pathway type
- menaquinol 8 biosynthesis
- Organism scope
Pathway network
55 nodes · 85 asserted directed edges
Arrows show recorded subject → object relationships, not necessarily metabolic flow. Select a node for details or an arrow for evidence. Scroll, zoom or find a node to explore.
- Reaction / activity
- Chemical / cofactor
- Protein / complex
- Cell / process context
- Pathway
- Solid arrow: mechanistic relation
- Dashed arrow: membership, location or cofactor relation
Components and activities
| Node | Kind or role | Source direction |
|---|---|---|
Escherichia coli K-12NCBITaxon:83333 | taxon | |
chorismate(2-)CHEBI:29748 | small molecule | |
isochorismate(2-)CHEBI:29780 | small molecule | |
2-oxoglutarate(2-)CHEBI:16810 | small molecule | |
hydronCHEBI:15378 | small molecule | |
(1R,2S,5S,6S)-2-(3-carboxylatopropanoyl)-5-[(1-carboxylatovinyl)oxy]-6-hydroxycyclohex-3-ene-1-carboxylateCHEBI:58818 | small molecule | |
carbon dioxideCHEBI:16526 | small molecule | |
(1R,6R)-2-(3-carboxylatopropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylateCHEBI:58689 | small molecule | |
pyruvateCHEBI:15361 | small molecule | |
2-succinatobenzoateCHEBI:18325 | small molecule | |
waterCHEBI:15377 | small molecule | |
ATP(4-)CHEBI:30616 | small molecule | |
coenzyme A(4-)CHEBI:57287 | small molecule | |
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA(5-)CHEBI:57364 | small molecule | |
adenosine 5'-monophosphate(2-)CHEBI:456215 | small molecule | |
diphosphate(3-)CHEBI:33019 | small molecule | |
1,4-dihydroxy-2-naphthoyl-CoA(4-)CHEBI:58897 | small molecule | |
1,4-dihydroxy-2-naphthoateCHEBI:11173 | small molecule | |
isopentenyl diphosphate(3-)CHEBI:128769 | small molecule | |
2-trans,6-trans-farnesyl diphosphate(3-)CHEBI:175763 | small molecule | |
all-trans-octaprenyl diphosphate(3-)CHEBI:57711 | small molecule | |
2-demethylmenaquinol-8CHEBI:61873 | lipid | |
S-adenosyl-L-methionine zwitterionCHEBI:59789 | small molecule | |
menaquinol-8CHEBI:61684 | lipid | |
S-adenosyl-L-homocysteine zwitterionCHEBI:57856 | small molecule | |
magnesium(2+)CHEBI:18420 | cofactor | |
manganese(2+)CHEBI:29035 | cofactor | |
thiamine(1+) diphosphate(3-)CHEBI:58937 | cofactor | |
hydrogencarbonateCHEBI:17544 | cofactor | |
plasma membraneGO:0005886 | cellular component | |
Isochorismate synthase MenFUniProtKB:P38051 | protein | |
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseUniProtKB:P17109 | protein | |
2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthaseUniProtKB:P37355 | protein | |
o-succinylbenzoate synthaseUniProtKB:P29208 | protein | |
2-succinylbenzoate--CoA ligaseUniProtKB:P37353 | protein | |
1,4-dihydroxy-2-naphthoyl-CoA synthaseUniProtKB:P0ABU0 | protein | |
1,4-dihydroxy-2-naphthoyl-CoA hydrolaseUniProtKB:P77781 | protein | |
Octaprenyl diphosphate synthaseUniProtKB:P0AD57 | protein | |
1,4-dihydroxy-2-naphthoate octaprenyltransferaseUniProtKB:P32166 | protein | |
Ubiquinone/menaquinone biosynthesis C-methyltransferase UbiEUniProtKB:P0A887 | protein | |
isochorismate synthase MenFMetaCyc:MENF-CPLX | complex | |
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 | complex | |
1,4-dihydroxy-2-naphthoyl-CoA synthaseMetaCyc:CPLX0-7882 | complex | |
1,4-dihydroxy-2-naphthoyl-CoA hydrolaseMetaCyc:CPLX0-8128 | complex | |
all-trans-octaprenyl-diphosphate synthaseMetaCyc:CPLX0-7426 | complex | |
chorismate => isochorismateRHEA:18986 | molecular activity | left to right |
isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 | molecular activity | left to right |
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 | molecular activity | left to right |
(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 | molecular activity | left to right |
2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | molecular activity | left to right |
2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 | molecular activity | left to right |
1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | molecular activity | left to right |
5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 | molecular activity | left to right |
all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | molecular activity | left to right |
2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 | molecular activity | left to right |
Mechanistic edges
| Subject | Predicate and description | Object | Evidence |
|---|---|---|---|
chorismate(2-)CHEBI:29748 | consumes | chorismate => isochorismateRHEA:18986 |
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chorismate => isochorismateRHEA:18986 | produces | isochorismate(2-)CHEBI:29780 |
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isochorismate(2-)CHEBI:29780 | consumes | isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 |
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2-oxoglutarate(2-)CHEBI:16810 | consumes | isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 |
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hydronCHEBI:15378 | consumes | isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 |
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isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 | produces | (1R,2S,5S,6S)-2-(3-carboxylatopropanoyl)-5-[(1-carboxylatovinyl)oxy]-6-hydroxycyclohex-3-ene-1-carboxylateCHEBI:58818 |
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isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 | produces | carbon dioxideCHEBI:16526 |
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(1R,2S,5S,6S)-2-(3-carboxylatopropanoyl)-5-[(1-carboxylatovinyl)oxy]-6-hydroxycyclohex-3-ene-1-carboxylateCHEBI:58818 | consumes | 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 |
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5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 | produces | (1R,6R)-2-(3-carboxylatopropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylateCHEBI:58689 |
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5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 | produces | pyruvateCHEBI:15361 |
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(1R,6R)-2-(3-carboxylatopropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylateCHEBI:58689 | consumes | (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 |
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(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 | produces | 2-succinatobenzoateCHEBI:18325 |
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(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 | produces | waterCHEBI:15377 |
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2-succinatobenzoateCHEBI:18325 | consumes | 2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 |
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ATP(4-)CHEBI:30616 | consumes | 2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 |
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coenzyme A(4-)CHEBI:57287 | consumes | 2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 |
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2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | produces | 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA(5-)CHEBI:57364 |
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2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | produces | adenosine 5'-monophosphate(2-)CHEBI:456215 |
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2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | produces | diphosphate(3-)CHEBI:33019 |
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4-(2-carboxyphenyl)-4-oxobutanoyl-CoA(5-)CHEBI:57364 | consumes | 2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 |
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hydronCHEBI:15378 | consumes | 2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 |
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2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 | produces | 1,4-dihydroxy-2-naphthoyl-CoA(4-)CHEBI:58897 |
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2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 | produces | waterCHEBI:15377 |
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1,4-dihydroxy-2-naphthoyl-CoA(4-)CHEBI:58897 | consumes | 1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 |
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waterCHEBI:15377 | consumes | 1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 |
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1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | produces | 1,4-dihydroxy-2-naphthoateCHEBI:11173 |
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1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | produces | coenzyme A(4-)CHEBI:57287 |
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1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | produces | hydronCHEBI:15378 |
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isopentenyl diphosphate(3-)CHEBI:128769 | consumes | 5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 |
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2-trans,6-trans-farnesyl diphosphate(3-)CHEBI:175763 | consumes | 5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 |
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5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 | produces | all-trans-octaprenyl diphosphate(3-)CHEBI:57711 |
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5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 | produces | diphosphate(3-)CHEBI:33019 |
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all-trans-octaprenyl diphosphate(3-)CHEBI:57711 | consumes | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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1,4-dihydroxy-2-naphthoateCHEBI:11173 | consumes | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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hydronCHEBI:15378 | consumes | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | produces | 2-demethylmenaquinol-8CHEBI:61873 |
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all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | produces | carbon dioxideCHEBI:16526 |
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all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | produces | diphosphate(3-)CHEBI:33019 |
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2-demethylmenaquinol-8CHEBI:61873 | consumes | 2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 |
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S-adenosyl-L-methionine zwitterionCHEBI:59789 | consumes | 2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 |
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2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 | produces | menaquinol-8CHEBI:61684 |
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2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 | produces | S-adenosyl-L-homocysteine zwitterionCHEBI:57856 |
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2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 | produces | hydronCHEBI:15378 |
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isochorismate synthase MenFMetaCyc:MENF-CPLX | catalyzes | chorismate => isochorismateRHEA:18986 |
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Isochorismate synthase MenFUniProtKB:P38051 | part_of | isochorismate synthase MenFMetaCyc:MENF-CPLX |
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isochorismate synthase MenFMetaCyc:MENF-CPLX | has_cofactor | magnesium(2+)CHEBI:18420 |
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chorismate => isochorismateRHEA:18986 | part_of | MetaCyc:PWY-5838 |
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2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 | catalyzes | isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 |
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2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseUniProtKB:P17109 | part_of | 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 |
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2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 | has_cofactor Metal alternatives do not imply simultaneous magnesium and manganese occupancy. | magnesium(2+)CHEBI:18420 |
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2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 | has_cofactor Metal alternatives do not imply simultaneous magnesium and manganese occupancy. | manganese(2+)CHEBI:29035 |
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2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseMetaCyc:CPLX0-7525 | has_cofactor | thiamine(1+) diphosphate(3-)CHEBI:58937 |
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isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 | part_of | MetaCyc:PWY-5838 |
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2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthaseUniProtKB:P37355 | catalyzes Monomeric MenH catalyzes the SHCHC-forming elimination; it is not assigned the later DHNA-CoA hydrolysis. | 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 |
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5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 | part_of | MetaCyc:PWY-5838 |
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o-succinylbenzoate synthaseUniProtKB:P29208 | enables Functional activity is represented without asserting isolated-monomer sufficiency. | (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 |
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o-succinylbenzoate synthaseUniProtKB:P29208 | has_cofactor | magnesium(2+)CHEBI:18420 |
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(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 | part_of | MetaCyc:PWY-5838 |
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2-succinylbenzoate--CoA ligaseUniProtKB:P37353 | enables Supported MenE function; native tetramer and reviewed homodimer-by-similarity assignments conflict, while inhibitor-bound author/PISA structures are monomeric. No unique oligomer is asserted. | 2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 |
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2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | part_of | MetaCyc:PWY-5838 |
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1,4-dihydroxy-2-naphthoyl-CoA synthaseMetaCyc:CPLX0-7882 | catalyzes | 2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 |
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1,4-dihydroxy-2-naphthoyl-CoA synthaseUniProtKB:P0ABU0 | part_of | 1,4-dihydroxy-2-naphthoyl-CoA synthaseMetaCyc:CPLX0-7882 |
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1,4-dihydroxy-2-naphthoyl-CoA synthaseMetaCyc:CPLX0-7882 | has_cofactor | hydrogencarbonateCHEBI:17544 |
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2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 | part_of | MetaCyc:PWY-5838 |
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1,4-dihydroxy-2-naphthoyl-CoA hydrolaseMetaCyc:CPLX0-8128 | catalyzes | 1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 |
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1,4-dihydroxy-2-naphthoyl-CoA hydrolaseUniProtKB:P77781 | part_of | 1,4-dihydroxy-2-naphthoyl-CoA hydrolaseMetaCyc:CPLX0-8128 |
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1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | part_of | MetaCyc:PWY-5838 |
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all-trans-octaprenyl-diphosphate synthaseMetaCyc:CPLX0-7426 | catalyzes | 5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 |
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Octaprenyl diphosphate synthaseUniProtKB:P0AD57 | part_of | all-trans-octaprenyl-diphosphate synthaseMetaCyc:CPLX0-7426 |
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all-trans-octaprenyl-diphosphate synthaseMetaCyc:CPLX0-7426 | has_cofactor The IspB magnesium assignment and two ions per subunit are by similarity. | magnesium(2+)CHEBI:18420 |
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5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 | part_of | MetaCyc:PWY-5838 |
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1,4-dihydroxy-2-naphthoate octaprenyltransferaseUniProtKB:P32166 | enables Functional activity is represented without asserting isolated-monomer sufficiency. | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | part_of | MetaCyc:PWY-5838 |
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Ubiquinone/menaquinone biosynthesis C-methyltransferase UbiEUniProtKB:P0A887 | enables Fixed-chain menaquinol methylation follows native and Rhea chemistry. The ubiquinone Ubi metabolon is not asserted as its required assembly here. | 2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 |
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2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 | part_of | MetaCyc:PWY-5838 |
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1,4-dihydroxy-2-naphthoate octaprenyltransferaseUniProtKB:P32166 | located_in | plasma membraneGO:0005886 |
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chorismate => isochorismateRHEA:18986 | provides_input_for Curated continuity through CHEBI:29780; no physical channeling or flux magnitude is asserted. | isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 |
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isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2RHEA:25594 | provides_input_for Curated continuity through CHEBI:58818; no physical channeling or flux magnitude is asserted. | 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 |
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5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvateRHEA:25598 | provides_input_for Curated continuity through CHEBI:58689; no physical channeling or flux magnitude is asserted. | (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 |
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(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2ORHEA:10197 | provides_input_for Curated continuity through CHEBI:18325; no physical channeling or flux magnitude is asserted. | 2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 |
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2-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphateRHEA:17010 | provides_input_for Curated continuity through CHEBI:57364; no physical channeling or flux magnitude is asserted. | 2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 |
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2-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2ORHEA:26563 | provides_input_for Curated continuity through CHEBI:58897; no physical channeling or flux magnitude is asserted. | 1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 |
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1,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+)RHEA:26310 | provides_input_for Curated continuity through CHEBI:11173; no physical channeling or flux magnitude is asserted. | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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5 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphateRHEA:27799 | provides_input_for Curated continuity through CHEBI:57711; no physical channeling or flux magnitude is asserted. | all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 |
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all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphateRHEA:30100 | provides_input_for Curated continuity through CHEBI:61873; no physical channeling or flux magnitude is asserted. | 2-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+)RHEA:30064 |
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References
RHEA:18986chorismate => isochorismate (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:25594isochorismate + 2-oxoglutarate + H(+) => 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2 (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:255985-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate => (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate + pyruvate (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:10197(1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate => 2-succinylbenzoate + H2O (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:170102-succinylbenzoate + ATP + CoA => 2-succinylbenzoyl-CoA + AMP + diphosphate (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:265632-succinylbenzoyl-CoA + H(+) => 1,4-dihydroxy-2-naphthoyl-CoA + H2O (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:263101,4-dihydroxy-2-naphthoyl-CoA + H2O => 1,4-dihydroxy-2-naphthoate + CoA + H(+) (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:277995 isopentenyl diphosphate + (2E,6E)-farnesyl diphosphate => all-trans-octaprenyl diphosphate + 5 diphosphate (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:30100all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H(+) => 2-demethylmenaquinol-8 + CO2 + diphosphate (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)RHEA:300642-demethylmenaquinol-8 + S-adenosyl-L-methionine => menaquinol-8 + S-adenosyl-L-homocysteine + H(+) (source version: Rhea 142, released 2026-09-02; digest covers full compressed RDF)UniProtKB:P38051Reviewed E. coli K-12 Isochorismate synthase MenF (source version: UniProt entry version 191, sequence version 4; retrieved 2026-10-11 UTC)MetaCyc:MENF-CPLXNative MENF-CPLX identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:9150206Menaquinone (vitamin K2) biosynthesis: overexpression, purification, and characterization of a new isochorismate synthase from Escherichia coli. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:MENF-MONOMERNative MENF-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:PWY-5838Native PWY-5838 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:PWY-5837Native PWY-5837 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:ISOCHORSYN-RXNNative ISOCHORSYN-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P17109Reviewed E. coli K-12 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase (source version: UniProt entry version 191, sequence version 4; retrieved 2026-10-11 UTC)MetaCyc:CPLX0-7525Native CPLX0-7525 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:17760421Menaquinone biosynthesis in Escherichia coli: identification of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate as a novel intermediate and re-evaluation of MenD activity. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:MEND-MONOMERNative MEND-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:14621995Steady-state kinetics and molecular evolution of Escherichia coli MenD [(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase], an anomalous thiamin diphosphate-dependent decarboxylase-carboligase. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:2.5.1.64-RXNNative 2.5.1.64-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P37355Reviewed E. coli K-12 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase (source version: UniProt entry version 171, sequence version 2; retrieved 2026-10-11 UTC)MetaCyc:EG12438-MONOMERNative EG12438-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:18284213Identification and characterization of (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase in the menaquinone biosynthesis of Escherichia coli. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:RXN-9310Native RXN-9310 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P29208Reviewed E. coli K-12 o-succinylbenzoate synthase (source version: UniProt entry version 193, sequence version 2; retrieved 2026-10-11 UTC)MetaCyc:O-SUCCINYLBENZOATE-COA-SYN-MONOMERNative O-SUCCINYLBENZOATE-COA-SYN-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:10978150Evolution of enzymatic activity in the enolase superfamily: structure of o-succinylbenzoate synthase from Escherichia coli in complex with Mg2+ and o-succinylbenzoate. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:O-SUCCINYLBENZOATE-COA-SYN-RXNNative O-SUCCINYLBENZOATE-COA-SYN-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P37353Reviewed E. coli K-12 2-succinylbenzoate--CoA ligase (source version: UniProt entry version 177, sequence version 2; retrieved 2026-10-11 UTC)MetaCyc:MENE-CPLXNative MENE-CPLX identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:26394156Mechanism of MenE inhibition by acyl-adenylate analogues and discovery of novel antibacterial agents. (source version: Primary article body inspected; retrieved 2026-10-11 UTC)MetaCyc:O-SUCCINYLBENZOATE-COA-LIG-RXNNative O-SUCCINYLBENZOATE-COA-LIG-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P0ABU0Reviewed E. coli K-12 1,4-dihydroxy-2-naphthoyl-CoA synthase (source version: UniProt entry version 146, sequence version 1; retrieved 2026-10-11 UTC)MetaCyc:CPLX0-7882Native CPLX0-7882 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:20643650A bicarbonate cofactor modulates 1,4-dihydroxy-2-naphthoyl-coenzyme a synthase in menaquinone biosynthesis of Escherichia coli. (source version: Primary article body inspected; retrieved 2026-10-11 UTC)MetaCyc:NAPHTHOATE-SYN-MONOMERNative NAPHTHOATE-SYN-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:NAPHTHOATE-SYN-RXNNative NAPHTHOATE-SYN-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P77781Reviewed E. coli K-12 1,4-dihydroxy-2-naphthoyl-CoA hydrolase (source version: UniProt entry version 172, sequence version 1; retrieved 2026-10-11 UTC)MetaCyc:CPLX0-8128Native CPLX0-8128 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:23564174Identification of a hotdog fold thioesterase involved in the biosynthesis of menaquinone in Escherichia coli. (source version: Primary article body inspected; retrieved 2026-10-11 UTC)MetaCyc:G6912-MONOMERNative G6912-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:25010423Structure and catalysis in the Escherichia coli hotdog-fold thioesterase paralogs YdiI and YbdB. (source version: Primary article body inspected; retrieved 2026-10-11 UTC)MetaCyc:RXN-9311Native RXN-9311 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P0AD57Reviewed E. coli K-12 Octaprenyl diphosphate synthase (source version: UniProt entry version 143, sequence version 1; retrieved 2026-10-11 UTC)MetaCyc:CPLX0-7426Native CPLX0-7426 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:8037730The identification of Escherichia coli ispB (cel) gene encoding the octaprenyl diphosphate synthase. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:OPPSYN-MONOMERNative OPPSYN-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:11108713Dimer formation of octaprenyl-diphosphate synthase (IspB) is essential for chain length determination of ubiquinone. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:PWY-5783Native PWY-5783 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:RXN-8992Native RXN-8992 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P32166Reviewed E. coli K-12 1,4-dihydroxy-2-naphthoate octaprenyltransferase (source version: UniProt entry version 170, sequence version 1; retrieved 2026-10-11 UTC)MetaCyc:DMK-MONOMERNative DMK-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:9573170Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli. (source version: Primary article body inspected; retrieved 2026-10-11 UTC)MetaCyc:PWY-5852Native PWY-5852 identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:DMK-RXNNative DMK-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)UniProtKB:P0A887Reviewed E. coli K-12 Ubiquinone/menaquinone biosynthesis C-methyltransferase UbiE (source version: UniProt entry version 158, sequence version 1; retrieved 2026-10-11 UTC)MetaCyc:2-OCTAPRENYL-METHOXY-BENZOQ-METH-MONOMERNative 2-OCTAPRENYL-METHOXY-BENZOQ-METH-MONOMER identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:9045837A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)MetaCyc:MENAQUINONESYN-PWYNative MENAQUINONESYN-PWY identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)MetaCyc:ADOMET-DMK-METHYLTRANSFER-RXNNative ADOMET-DMK-METHYLTRANSFER-RXN identity and mechanism (source version: MetaCyc 22.5; complete native XML retrieved 2026-10-11 UTC)PMID:9795253The role of isochorismate hydroxymutase genes entC and menF in enterobactin and menaquinone biosynthesis in Escherichia coli. (source version: Europe PMC indexed primary abstract inspected; full text not claimed; retrieved 2026-10-11 UTC)PMID:23637813Crystal Structures of E. coli Native MenH and Two Active Site Mutants (source version: Primary article body inspected; retrieved 2026-10-11 UTC)DOI:10.2210/pdb6NJ0/pdbRCSB biological assembly 1 for 6NJ0 wild-type E. coli MenE with a bound inhibitor analogue (source version: Original RCSB assembly JSON retrieved 2026-10-11 UTC; inhibitor-bound structural context)DOI:10.2210/pdb5C5H/pdbRCSB biological assembly 1 for 5C5H R195K E. coli MenE with bound OSB-AMS (source version: Original RCSB assembly JSON retrieved 2026-10-11 UTC; inhibitor-bound structural context)PMID:30912442Structure-Based Design, Synthesis, and Biological Evaluation of Non-Acyl Sulfamate Inhibitors of the Adenylate-Forming Enzyme MenE (source version: 2019; complete primary HTML retrieved 2026-10-11 UTC; inspected Methods P17 and Results P32)
Curation history
- codex
- CREATE — Curated complete MetaCyc:PWY-5838 pathway network
Complete ten-reaction native boundary including octaprenyl donor branch; fixed-chain quinol chemistry, MenF identity, and unresolved MenE assembly are explicitly retained. Record SHA256 895c30975dd0297d29ae6fa123ba8566d79a99d247e236a611a8633eaf7b0b50. Evidence bodies, exact replays and source dispositions are retained in research/pathway_additions/2026-10-11-next-195. Shared authority integration, generated pages, full local gates and independent scientific reviews are subsequent checks; this CREATE event does not claim their completion.
- CREATE — Curated complete MetaCyc:PWY-5838 pathway network
- codex
- EDIT — Ground the retained MenE assembly conflict in direct structure evidence
Added two exact RCSB assembly evidence/reference entries for the already-stated monomeric inhibitor-structure contrast; no nodes, reactions or chemical sides changed. Final author-frozen YAML SHA256 ce7ca7155a12be396ea94b0b83c5b6ca72285c1cf53188fb1916e559c7e15e81. This succeeds the initial CREATE observation history/records/superpathway-of-menaquinol-8-biosynthesis-i/2026-10-11T061040Z-codex-f03795.yaml. The independent scientific review and shared gates are subsequent checks.
- EDIT — Ground the retained MenE assembly conflict in direct structure evidence
- codex
- EDIT — Correct menaquinol primary locators and MenE source attribution
Addressed independent findings menaquinol-primary-section-locators and menaquinol-mene-structure-context-attribution. Eight primary section pointers now match original bodies. Two assembly JSON assertions are restricted to actual assembly fields; two separate primary assertions supply exact MenE mutation/protein/ligand context. Initial and intermediate input archives preserve reviewed bytes and both canonical observations. Final YAML SHA256 a9a1d571791078e1286e57ad686df30579254adf9ab0f5590d93e09757190f42; 85 edges and 181 evidence items, with unchanged nodes and chemistry. Complete chemistry replay passed on the intermediate record; focused exact source/hash/schema/KGX checks passed on the final delta. Final independent successor and shared corpus gates follow.
- EDIT — Correct menaquinol primary locators and MenE source attribution
- Codex
- EDIT — Remove three nonexistent redundant cofactor JSON pointers
Resolved issue361 by removing only /comments/2/note from menaquinol edges050,051,057. Exact native UniProt P17109/P29208 cofactor objects retain the asserted ChEBI/ECO evidence. Archived reviewed inputs under research/pathway_additions/2026-10-11-next-195/pre-pointer-review-inputs. Target a9a1d571791078e1286e57ad686df30579254adf9ab0f5590d93e09757190f42 becomes8d24e6ff858759aa4eaecd04b456ffa1b79c992bc090637f5cc8805a5ecbf492. Focused author replay confirms only these three locators differ;85edges181evidence68references and all actual KGX non-evidence fields/nodes unchanged. Native/closed schema and source digest checks pass. Prior full chemistry replay retained; root shared post-pointer checks and independent successor review are separately recorded.
- EDIT — Remove three nonexistent redundant cofactor JSON pointers