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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 15:12:23 UTC
Update Date2021-09-14 15:47:24 UTC
Secondary Accession Numbers
  • HMDB0062451
  • HMDB02972
  • HMDB62451
Metabolite Identification
Common NameVitamin K1 2,3-epoxide
DescriptionVitamin K1 2,3-epoxide (CAS: 25486-55-9) is a vitamin K derivative. Vitamin K is 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 into gamma-carboxyglutamate (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 into 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 into 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 the coumarin-like activity of drugs (PMID: 2401753 ).
Phylloquinone oxideHMDB
Phylloquinone epoxideHMDB
Vitamin K1 oxideHMDB
Vitamin K epoxideHMDB
Vitamin K(1) oxideHMDB
Vitamin K1 epoxideHMDB
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinoneHMDB
Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxideHMDB
Phylloquinone, epoxideHMDB
Vitamin K 2,3-epoxideHMDB
Vitamin K1, epoxideHMDB
Phylloquinone 2,3-epoxideHMDB
Vitamin K oxideHMDB
Vitamin K1 2,3-epoxideHMDB
Chemical FormulaC31H46O3
Average Molecular Weight466.706
Monoisotopic Molecular Weight466.344695341
IUPAC Name(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione
Traditional Name(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphtho[2,3-b]oxirene-2,7-dione
CAS Registry Number85955-78-8
InChI Identifier
Chemical Taxonomy
Description 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
  • 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 DescriptorsNot Available

Biological location


Route of exposure


Naturally occurring process

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
Water Solubility2.2e-05 g/LALOGPS
logP10(8.28) g/LALOGPS
logP10(9.22) g/LChemAxon
logS10(-7.3) 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
Polarizability56.23 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin K1 2,3-epoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 10V, Negative-QTOFsplash10-014i-0000900000-34d4a26fdf7a1cd267302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 20V, Negative-QTOFsplash10-014r-0200900000-9ed845fe28276c1a26402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 40V, Negative-QTOFsplash10-004r-0209100000-2b233ea9a16eecb885222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 10V, Positive-QTOFsplash10-014i-0012900000-5563789bc0b75fbe920c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 20V, Positive-QTOFsplash10-0a4j-9730300000-4af0219041341f3904b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 40V, Positive-QTOFsplash10-0002-9711000000-82abc89ed052cf2ea5702021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023087
KNApSAcK IDNot Available
Chemspider ID34993195
KEGG Compound IDC05849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound5280845
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 + 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:
Uniprot ID:
Molecular weight:
Phylloquinol + Oxidized dithiothreitol → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails
Vitamin K1 + Oxidized dithiothreitol + Water → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails