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Record Information
Version3.6
Creation Date2006-05-22 15:12:23 UTC
Update Date2016-02-11 01:05:56 UTC
HMDB IDHMDB02972
Secondary Accession NumbersNone
Metabolite Identification
Common NameVitamin K1 2,3-epoxide
DescriptionVitamin K1 2,3-epoxide is a vitamin K derivative. Vitamin K needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Within the cell, Vitamin K undergoes electron reduction to a reduced form of Vitamin K (called Vitamin K hydroquinone) by the enzyme Vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes Vitamin K hydroquinone to allow carboxylation of Glutamate to Gamma-cabroxygluatmate (Gla); this enzyme is called the gamma-glutamyl carboxylase or the Vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize Vitamin K hydroquinone to vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted to Vitamin K by the Vitamin K epoxide reductase. These two enzymes comprise the so-called Vitamin K cycle. One of the reasons why Vitamin K is rarely deficient in a human diet is because Vitamin K is continually recycled in our cells. Vitamin K 2,3-epoxide is the substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Significantly increased level of serum vitamin K epoxide has been found in patients with familial multiple coagulation factor deficiency. (PMID 12384421 ) Accumulation of vitamin K1-2,3-epoxide in plasma is also a sensitive marker of coumarin-like activity of drugs. (PMID 2401753 ).
Structure
Thumb
Synonyms
ValueSource
(2,3-Epoxyphytyl)menaquinoneChEBI
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinoneChEBI
1a,7a-dihydro-1a-Methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dioneChEBI
2,3-Epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinoneChEBI
2,3-EpoxyphylloquinoneChEBI
Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxideChEBI
Phylloquinone epoxideChEBI
Phylloquinone oxideChEBI
Phylloquinone, epoxideChEBI
Phylloquinone-2,3-epoxideChEBI
Vitamin K 2,3-epoxideChEBI
Vitamin K1 2,3-epoxideChEBI
Vitamin K1 oxideChEBI
Vitamin K1, epoxideChEBI
Phylloquinone 2,3-epoxideHMDB
Chemical FormulaC31H46O3
Average Molecular Weight466.6951
Monoisotopic Molecular Weight466.344695338
IUPAC Name1a-methyl-7a-(3,7,11,15-tetramethylhexadec-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione
Traditional Namevitamin k epoxide
CAS Registry Number25486-55-9
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O
InChI Identifier
InChI=1S/C31H46O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+
InChI KeyInChIKey=KUTXFBIHPWIDJQ-LKUDQCMESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentVitamin K compounds
Alternative Parents
Substituents
  • Diterpenoid
  • Naphthoquinone
  • Tetralin
  • Naphthalene
  • Aryl alkyl ketone
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.24e-05 mg/mLALOGPS
logP8.28ALOGPS
logP9.22ChemAxon
logS-7.3ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.67 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity141.69 m3·mol-1ChemAxon
Polarizability57.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Vitamin K MetabolismSMP00464Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000021 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023087
KNApSAcK IDNot Available
Chemspider ID4444391
KEGG Compound IDC05849
BioCyc ID23-EPOXY-23-DIHYDRO-2-METHYL-14-NAPHTHOQ
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02972
Metagene LinkHMDB02972
METLIN ID3030
PubChem Compound5280845
PDB IDNot Available
ChEBI ID177881
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Komatsu K, Kayashima N, Ariyoshi N, Shirahata A: [Vitamin K] Nippon Rinsho. 1993 Apr;51(4):943-51. [8483276 ]
  2. Hirauchi K, Sakano T, Nagaoka T, Morimoto A: Simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide and menaquinone-4 in human plasma by high-performance liquid chromatography with fluorimetric detection. J Chromatogr. 1988 Aug 19;430(1):21-9. [2851012 ]
  3. McBurney A, Shearer MJ, Barkhan P: Changes in the urinary metabolites of phylloquinone (vitamin K1) in man following therapeutic anticoagulation with warfarin. Biochem Pharmacol. 1978 Feb 1;27(3):273-8. [619911 ]
  4. Fregin A, Rost S, Wolz W, Krebsova A, Muller CR, Oldenburg J: Homozygosity mapping of a second gene locus for hereditary combined deficiency of vitamin K-dependent clotting factors to the centromeric region of chromosome 16. Blood. 2002 Nov 1;100(9):3229-32. [12384421 ]
  5. Trenk D, Wagner F, Bechtold H, Nies B, Jahnchen E: Lack of effect of cefixime on the metabolism of vitamin K1. J Clin Pharmacol. 1990 Aug;30(8):737-42. [2401753 ]

Enzymes

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 + Reduced Vitamin K (phylloquinone)details
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
Reduced Vitamin K (phylloquinone) + Oxidized dithiothreitol → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails
Vitamin K1 + Oxidized dithiothreitol + Water → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails