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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: menaquinone-1

Synonyms: Vitamin MK 1, 2-methyl-3-(3-methyl-2-butenyl)naphthoquinone, Lepachol acetate

Superclasses: a redox electron carrier Membrane-Electron-Carriers an electron-transfer-related quinone a menaquinone
a vitamin a vitamin K a menaquinone
an aldehyde or ketone a ketone a cyclic ketone a quinone an electron-transfer-related quinone a menaquinone

Chemical Formula: C16H16O2

Molecular Weight: 240.3 Daltons

Monoisotopic Molecular Weight: 240.1150297578 Daltons

SMILES: CC(C)=CCC1(C(=O)C2(C(C(=O)C(C)=1)=CC=CC=2))

InChI: InChI=1S/C16H16O2/c1-10(2)8-9-12-11(3)15(17)13-6-4-5-7-14(13)16(12)18/h4-8H,9H2,1-3H3

InChIKey: InChIKey=ABSPRNADVQNDOU-UHFFFAOYSA-N

Unification Links: ChEBI:25185 , ChemSpider:243055 , PubChem:276204

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 153.46793 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

formate to dimethyl sulfoxide electron transfer , formate to trimethylamine N-oxide electron transfer , nitrate reduction III (dissimilatory) :
formate[periplasmic space] + a menaquinone[inner membrane] + 2 H+ → CO2[periplasmic space] + a menaquinol[inner membrane] + H+[periplasmic space]

glycerol-3-phosphate to fumarate electron transfer :
sn-glycerol 3-phosphate + a menaquinone[inner membrane] → dihydroxyacetone phosphate + a menaquinol[inner membrane]

heme biosynthesis II (anaerobic) :
protoporphyrinogen IX + 3 a menaquinone → protoporphyrin IX + 3 a menaquinol

NADH to dimethyl sulfoxide electron transfer , NADH to fumarate electron transfer , NADH to trimethylamine N-oxide electron transfer , nitrate reduction VIII (dissimilatory) :
NADH + a menaquinone[inner membrane] + 5 H+ → NAD+ + a menaquinol[inner membrane] + 4 H+[periplasmic space]

sulfite oxidation V (SoeABC) :
sulfite + a menaquinone + H2O → sulfate + a menaquinol

TCA cycle VIII (helicobacter) :
(S)-malate + a menaquinone → oxaloacetate + a menaquinol

Not in pathways:
(S)-dihydroorotate + a menaquinone[inner membrane] → orotate + a menaquinol[inner membrane]
a menaquinone[inner membrane] + 2 H+ + H2[periplasmic space] → a menaquinol[inner membrane] + 2 H+[periplasmic space]

(5R)-carbapenem carboxylate biosynthesis , citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , proline degradation :
L-proline + an electron-transfer-related quinone[inner membrane] → (S)-1-pyrroline-5-carboxylate + an electron-transfer-related quinol[inner membrane] + H+

4-hydroxymandelate degradation :
(S)-4-hydroxymandelate + an electron-transfer-related quinone → 2-(4-hydroxyphenyl)-2-oxoacetate + an electron-transfer-related quinol

alanine degradation I :
D-alanine + an electron-transfer-related quinone[inner membrane] + H2O → ammonium + pyruvate + an electron-transfer-related quinol[inner membrane]

sulfide oxidation I (sulfide-quinone reductase) :
hydrogen sulfide + an electron-transfer-related quinone → intracellular S0 + an electron-transfer-related quinol

TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) , TCA cycle VII (acetate-producers) :
succinate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] → fumarate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]

trans-4-hydroxy-L-proline degradation I :
trans-4-hydroxy-L-proline[in] + an electron-transfer-related quinone → pyrroline-hydroxy-carboxylate[in] + an electron-transfer-related quinol + H+[in]

trans-lycopene biosynthesis II (plants) :
7,9,9'-cis-neurosporene + an electron-transfer-related quinone → prolycopene + an electron-transfer-related quinol
9,9'-di-cis-ζ-carotene + an electron-transfer-related quinone → 7,9,9'-cis-neurosporene + an electron-transfer-related quinol


(S)-dihydroorotate + an electron-transfer-related quinone[inner membrane] → orotate + an electron-transfer-related quinol[inner membrane]
NADPH + an electron-transfer-related quinone + H+ → NADP+ + an electron-transfer-related quinol
a D-amino acid[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]
D-glucopyranose[out] + an electron-transfer-related quinone + 2 H+[in] → D-glucono-1,5-lactone[out] + an electron-transfer-related quinol + 2 H+[out]
sn-glycerol 3-phosphate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] → dihydroxyacetone phosphate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]

quinate degradation I :
L-quinate + a quinone → 3-dehydroquinate + a quinol

shikimate degradation I :
shikimate + a quinone → 3-dehydroshikimate + a quinol

TCA cycle I (prokaryotic) , TCA cycle VII (acetate-producers) :
(S)-malate + a quinone → oxaloacetate + a quinol

thiosulfate oxidation II (to tetrathionate) :
2 thiosulfate + a quinone → tetrathionate + a quinol


a quinone + NAD(P)H + H+ → a quinol + NAD(P)+
a cyclic alcohol + a quinonea cyclic ketone + a quinol


a cyclic alcohol + a quinonea cyclic ketone + a quinol

Reactions known to produce the compound:

formate to dimethyl sulfoxide electron transfer , NADH to dimethyl sulfoxide electron transfer :
dimethyl sulfoxide[periplasmic space] + a menaquinol[inner membrane] → dimethyl sulfide[periplasmic space] + a menaquinone[inner membrane] + H2O[periplasmic space]

formate to trimethylamine N-oxide electron transfer , NADH to trimethylamine N-oxide electron transfer :
trimethylamine N-oxide[periplasmic space] + a menaquinol[inner membrane] + H+[periplasmic space] → trimethylamine[periplasmic space] + a menaquinone[inner membrane] + H2O[periplasmic space]

nitrate reduction III (dissimilatory) , nitrate reduction VIII (dissimilatory) :
nitrate + a menaquinol[inner membrane] + 2 H+ → nitrite + a menaquinone[inner membrane] + H2O + 2 H+[periplasmic space]

nitrate reduction VII (denitrification) :
2 nitric oxide + a menaquinol → nitrous oxide + a menaquinone + H2O

Not in pathways:
2 an oxidized c-type cytochrome[out] + a menaquinol → 2 a reduced c-type cytochrome[out] + a menaquinone + 2 H+[in]
2 a menaquinol + oxygen[in] + 8 H+[in] → 2 a menaquinone + 8 H+[out] + 2 H2O[in]
S-adenosyl-L-methionine + a demethylmenaquinone → S-adenosyl-L-homocysteine + a menaquinone

methane oxidation to methanol II :
methane + an electron-transfer-related quinol + oxygen → methanol + an electron-transfer-related quinone + H2O

TCA cycle VI (obligate autotrophs) :
succinate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] ← fumarate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]


2 an oxidized c-type cytochrome[out] + an electron-transfer-related quinol → 2 a reduced c-type cytochrome[out] + an electron-transfer-related quinone + 2 H+[in]

cuticular wax biosynthesis :
a secondary alcohol + an oxidized electron acceptor → a ketone + a reduced electron acceptor


a secondary alcohol + oxygen → a ketone + hydrogen peroxide


a nitroalkane + oxygen + H2O → an aldehyde or ketone + nitrite + hydrogen peroxide + H+

Reactions known to both consume and produce the compound:

glycerol-3-phosphate to fumarate electron transfer , incomplete reductive TCA cycle , mixed acid fermentation , NADH to fumarate electron transfer , pyruvate fermentation to propionate I , reductive TCA cycle I , reductive TCA cycle II , TCA cycle VIII (helicobacter) :
fumarate[in] + a menaquinol[CCO-OUT-CCO-IN] ↔ succinate[in] + a menaquinone[CCO-OUT-CCO-IN]

nitrate reduction I (denitrification) , nitrate reduction VII (denitrification) :
nitrate[in] + an electron-transfer-related quinol ↔ nitrite[in] + an electron-transfer-related quinone + H2O[in]

Not in pathways:
a quinone + NADPH ↔ a semiquinone + NADP+

In Reactions of unknown directionality:

Not in pathways:
a menaquinone + H2 = a menaquinol


9,9'-di-cis-ζ-carotene + 2 an electron-transfer-related quinone = prolycopene + 2 an electron-transfer-related quinol
formate + an electron-transfer-related quinone + H+ = CO2 + an electron-transfer-related quinol
NADH + an electron-transfer-related quinone + H+ = NAD+ + an electron-transfer-related quinol
an (R)-2-hydroxyacid + an electron-transfer-related quinone = a 2-oxo acid + an electron-transfer-related quinol
an oxidized coenzyme F420 + an electron-transfer-related quinol = a reduced coenzyme F420 + an electron-transfer-related quinone


phenylacetyl-CoA + 2 a quinone + H2O = 2 a quinol + phenylglyoxylyl-CoA
a quinone + NADH = a semiquinone + NAD+
1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ = a quinol + 1-(β-D ribofuranosyl)nicotinamide


a ketone + NADP+ = an enone + NADPH + H+
a secondary alcohol + an oxidized coenzyme F420 = a ketone + a reduced coenzyme F420
a secondary alcohol + NADP+ = a ketone + NADPH + H+
a secondary alcohol + NAD+ = a ketone + NADH + H+

In Redox half-reactions:
a menaquinone + 2 H+[out] + 2 e- → a menaquinol ,
a menaquinone + 2 H+[in] + 2 e- → a menaquinol ,
an electron-transfer-related quinone + 2 H+[in] + 2 e- → an electron-transfer-related quinol

Enzymes inhibited by menaquinone-1, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: succinate:quinone oxidoreductase

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: putrescine oxidase


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, biocyc14.