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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 quinol
a vitamin a vitamin K
an aromatic compound a quinol an electron-transfer 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: C31H48O2

Molecular Weight: 452.72 Daltons

Monoisotopic Molecular Weight: 452.365430785 Daltons

phylloquinol compound structure

SMILES: CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC2(C(=C(O)C1(C=CC=CC=1C=2O))C)

InChI: InChI=1S/C31H48O2/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/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

InChIKey: InChIKey=BUFJIHPUGZHTHL-NKFFZRIASA-N

Unification Links: PubChem:49859693

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 495.52478 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
vitamin K 2,3-epoxide + a [protein] 4-carboxy-L-glutamate + H+ + H2O ← phylloquinol + a [protein]-α-L-glutamate + CO2 + oxygen

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

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

Not in pathways:
2 an oxidized c-type cytochrome[out] + an electron-transfer quinol[membrane] → 2 a reduced c-type cytochrome[out] + an electron-transfer quinone[membrane] + 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 , L-citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , L-proline degradation :
L-proline + an electron-transfer quinone[inner membrane] → (S)-1-pyrroline-5-carboxylate + an electron-transfer quinol[inner membrane] + H+

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

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

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

TCA cycle I (prokaryotic) :
(S)-malate[in] + an electron-transfer quinone[membrane] → oxaloacetate[in] + an electron-transfer quinol[membrane]

TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) :
succinate[in] + an electron-transfer quinone[membrane] → fumarate[in] + an electron-transfer quinol[membrane]

TCA cycle VII (acetate-producers) :
(S)-malate[in] + an electron-transfer quinone[membrane] → oxaloacetate[in] + an electron-transfer quinol[membrane]
succinate[in] + an electron-transfer quinone[membrane] → fumarate[in] + an electron-transfer quinol[membrane]

trans-4-hydroxy-L-proline degradation I :
trans-4-hydroxy-L-proline[in] + an electron-transfer quinone[membrane] → (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate[in] + an electron-transfer quinol[membrane] + H+[in]

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

UMP biosynthesis :
(S)-dihydroorotate + an electron-transfer quinone[inner membrane] → orotate + an electron-transfer quinol[inner membrane]

Not in pathways:
NADPH[in] + an electron-transfer quinone[membrane] + H+[in] → NADP+[in] + an electron-transfer quinol[membrane]
an electron-transfer quinone[membrane] + NAD(P)H[in] + H+[in]an electron-transfer quinol[membrane] + NAD(P)+[in]
sn-glycerol 3-phosphate[in] + an electron-transfer quinone[membrane] → glycerone phosphate[in] + an electron-transfer quinol[membrane]
D-glucopyranose[out] + an electron-transfer quinone[membrane] + 2 H+[in] → D-glucono-1,5-lactone[out] + an electron-transfer quinol[membrane] + 2 H+[out]
a D-amino acid[in] + an electron-transfer quinone[membrane] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer quinol[membrane]

phenylacetate degradation II (anaerobic) :
phenylacetyl-CoA + 2 a quinone + H2O → 2 a quinol + phenylglyoxylyl-CoA

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

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

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

Not in pathways:
a cyclic alcohol + a quinone → a cyclic ketone + a quinol

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

Not in pathways:
an oxidized coenzyme F420 + an electron-transfer quinol = a reduced coenzyme F420 + an electron-transfer quinone
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
an (R)-2-hydroxyacid + an electron-transfer quinone = a 2-oxo acid + an electron-transfer quinol
NADH + an electron-transfer quinone + H+ = NAD+ + an electron-transfer quinol
formate + an electron-transfer quinone + H+ = CO2 + an electron-transfer quinol
9,9'-di-cis-ζ-carotene + 2 an electron-transfer quinone = prolycopene + 2 an electron-transfer quinol

Not in pathways:
1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ = a quinol + 1-(β-D ribofuranosyl)nicotinamide

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

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


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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 19.0 on Sun Apr 19, 2015, biocyc12.