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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: phylloquinone

Synonyms: 2-methyl-3-phytyl-1,4-naphthoquinone, phytonadione, phytomenadione, 3-phytylmenadione, vitamin K1

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

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. It is an electron acceptor in the electron transport chain of chloroplasts.

Chemical Formula: C31H46O2

Molecular Weight: 450.7 Daltons

Monoisotopic Molecular Weight: 450.34978072079997 Daltons

SMILES: CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC2(=C(C(=O)C1(C=CC=CC=1C2=O))C)

InChI: InChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+

InChIKey: InChIKey=MBWXNTAXLNYFJB-LKUDQCMESA-N

Unification Links: CAS:84-80-0 , ChEBI:583972 , ChemSpider:4444124 , HMDB:HMDB03555 , KEGG:C02059 , NCI:270681 , PubChem:5280483 , Wikipedia:Phylloquinone

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 480.47156 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
phylloquinone + a reduced electron acceptor + oxygen → vitamin K 2,3-epoxide + an oxidized electron acceptor + H2O

(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:

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]

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:

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:
vitamin K 2,3-epoxide + a [protein] 4-carboxy-L-glutamate + H2O = phylloquinone + a [protein]-α-L-glutamate + CO2 + oxygen + H+
phylloquinone + oxidized dithiothreitol + H2O = dithiothreitol + vitamin K 2,3-epoxide
phylloquinone + NADPH + H+ + oxygen = ω-hydroxyphylloquinone + NADP+ + H2O


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:
an electron-transfer-related quinone + 2 H+[in] + 2 e- → an electron-transfer-related quinol

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

Credits:
Revised 02-Jul-2009 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 Wed Dec 17, 2014, BIOCYC14B.