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Record Information
Creation Date2006-05-22 15:12:23 UTC
Update Date2017-09-27 08:24:18 UTC
Secondary Accession Numbers
  • HMDB02972
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 ).
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-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
Vitamin K 2,3-epoxideChEBI
Vitamin K1 oxideChEBI
Vitamin K1, epoxideChEBI
Phylloquinone 2,3-epoxideHMDB
Vitamin K epoxideHMDB
Vitamin K(1) oxideMeSH
Vitamin K1 epoxideMeSH
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentVitamin K compounds
Alternative Parents
  • Diterpenoid
  • Naphthoquinone
  • Naphthalene
  • Tetralin
  • Quinone
  • Aryl ketone
  • Aryl alkyl ketone
  • Benzenoid
  • Ketone
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Biological Location:


  Biofluid and excreta:




Route of exposure:



Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility2.2e-05 g/LALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.67 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity141.69 m³·mol⁻¹ChemAxon
Polarizability57.54 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0130900000-3b1bc358b43e27854bb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ktk-5690300000-ece538d0d9bd3857484aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9880100000-4aeb98e31bc2eec7a7cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-d7ac14f3da074ab1a0a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0010900000-f6d434f05e8f2c7c56dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-6891300000-6a0524a63604098eb1bfView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Acenocoumarol PathwayPw000312Pw000312 greyscalePw000312 simpleNot Available
Alteplase PathwayPw000302Pw000302 greyscalePw000302 simpleNot Available
Aminocaproic Acid PathwayPw000308Pw000308 greyscalePw000308 simpleNot Available
Anistreplase PathwayPw000303Pw000303 greyscalePw000303 simpleNot Available
Aprotinin PathwayPw000310Pw000310 greyscalePw000310 simpleNot Available
Displaying entries 1 - 5 of 25 in total
Normal Concentrations
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
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound5280845
PDB IDNot Available
ChEBI ID177881
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Komatsu K, Kayashima N, Ariyoshi N, Shirahata A: [Vitamin K]. Nihon Rinsho. 1993 Apr;51(4):943-51. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:2401753 ]


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:
Uniprot ID:
Molecular weight:
[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:
Uniprot ID:
Molecular weight:
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