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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 14:02:40 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004198
Secondary Accession Numbers
  • HMDB0060502
  • HMDB04198
  • HMDB60502
Metabolite Identification
Common NamePhylloquinol
DescriptionPhylloquinol, also known as vitamin K1 hydroquinone or reduced vitamin K1, is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione).
Structure
Thumb
Synonyms
Chemical FormulaC31H48O2
Average Molecular Weight452.7116
Monoisotopic Molecular Weight452.36543078
IUPAC Name2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-diol
Traditional Namevitamin K hydroquinone
CAS Registry Number572-96-3
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C
InChI Identifier
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
InChI KeyBUFJIHPUGZHTHL-NKFFZRIASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Prenylbenzoquinol
  • 1-naphthol
  • Naphthalene
  • Hydroquinone
  • Benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031116
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03313
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280585
PDB IDNot Available
ChEBI ID28433
Food Biomarker OntologyNot Available
VMH IDM02829
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMasaki, Yukio; Hashimoto, Kinji; Kaji, Kenji. Synthetic studies on isoprenoidquinones. II. Syntheses of ubiquinone-10, phylloquinone, and menaquinone-4 by a chain-extending method utilizing terminally functionalized isoprenoidhydroquinones. Chemical & Pharmaceutical Bulletin (1984), 32(10), 3959-67.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tovar A, Ameho CK, Blumberg JB, Peterson JW, Smith D, Booth SL: Extrahepatic tissue concentrations of vitamin K are lower in rats fed a high vitamin E diet. Nutr Metab (Lond). 2006 Jul 20;3:29. [PubMed:16857056 ]
  2. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular weight:
30867.405
Reactions
Vitamin K1 + NADH + Hydrogen Ion → Phylloquinol + NADdetails
General function:
Involved in gamma-glutamyl carboxylase activity
Specific function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular weight:
87560.065
Reactions
[Peptidyl]-4-carboxyglutamate + Vitamin K1 2,3-epoxide + Water → [peptidyl]-glutamate + CO(2) + Oxygen + Phylloquinoldetails
Gla protein + Vitamin K1 2,3-epoxide + Water → Gla protein precursor + Phylloquinol + Carbon dioxide + Oxygendetails
General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
Reactions
Phylloquinol + Oxidized dithiothreitol → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails