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MetaCyc Compound: phylloquinol

Synonyms: 2-methyl-3-phytyl-1,4-naphthoquinol

Superclasses: a redox electron carrier Membrane-Electron-Carriers an electron-transfer-related quinol
a vitamin a vitamin K
an aromatic compound a quinol an electron-transfer-related quinol

Summary:
Vitamin K is a name given to a group of derivatives of 2-methyl-1,4-naphthoquinone that are required by mammals for the posttranslational modification of certain proteins, mostly involved in blood coagulation. These compounds, while essential for mammals, are not synthesized by them, and are thus considered vitamins.

The natural forms of the vitamin are vitamin K1 (phylloquinone) and vitamin K2 (a menaquinone). Since menaquinones produced by different organisms have different tail lenghts, there are many variations of vitamin K2, usually specified based on the number of carbons in their tails, such as in Vitamin K2(45). Menaquinones are synthesized by gut bacteria, and are absorbed into the blood. Thus, dietary deficiency is extremely rare in healthy individuals.

phylloquinone is found naturally in a wide variety of green plants and cyanobacteria, and contains a phytyl side chain.

Chemical Formula: C31H50O2

Molecular Weight: 454.74 Daltons

Monoisotopic Molecular Weight: 454.3810808492 Daltons

SMILES: CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC2(=C(C(O)C1(C=CC=CC=1C2O))C)

InChI: InChI=1S/C31H50O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,30-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-,30?,31?/m1/s1

InChIKey: InChIKey=QCSGFVIGSQVCCX-HBDFACPTSA-N

Unification Links: PubChem:49859693

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 511.53607 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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]

Not in pathways:
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]

Reactions known to produce the compound:

phylloquinol biosynthesis :
demethylphylloquinol + S-adenosyl-L-methionine → phylloquinol + S-adenosyl-L-homocysteine + H+

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

Not in pathways:
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]
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]
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]
NADPH + an electron-transfer-related quinone + H+ → NADP+ + an electron-transfer-related quinol
(S)-dihydroorotate + an electron-transfer-related quinone[inner membrane] → orotate + an electron-transfer-related quinol[inner membrane]

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

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

Not in pathways:
an oxidized coenzyme F420 + an electron-transfer-related quinol = a reduced coenzyme F420 + an electron-transfer-related quinone
an (R)-2-hydroxyacid + an electron-transfer-related quinone = a 2-oxo acid + an electron-transfer-related quinol
NADH + an electron-transfer-related quinone + H+ = NAD+ + an electron-transfer-related quinol
formate + an electron-transfer-related quinone + H+ = CO2 + an electron-transfer-related quinol
9,9'-di-cis-ζ-carotene + 2 an electron-transfer-related quinone = prolycopene + 2 an electron-transfer-related quinol


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

In Redox half-reactions:
an electron-transfer-related quinone + 2 H+[in] + 2 e-an electron-transfer-related quinol

Credits:
Created 10-Nov-2010 by Caspi R , SRI International


References

Collins81: Collins MD, Jones D (1981). "Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implication." Microbiol Rev 45(2);316-54. PMID: 7022156

Fujimoto12: Fujimoto N., Kosaka T., Yamada M. (2012). "Menaquinone as Well as Ubiquinone as a Crucial Component in the Escherichia coli Respiratory Chain." Chapter 10 in Chemical Biology, edited by D Ekinci, ISBN 978-953-51-0049-2.

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

Shimada01: Shimada H, Shida Y, Nemoto N, Oshima T, Yamagishi A (2001). "Quinone profiles of Thermoplasma acidophilum HO-62." J Bacteriol 183(4);1462-5. PMID: 11157962


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 Fri Nov 21, 2014, BIOCYC14A.