Record Information
Version1.0
Creation date2011-09-21 00:24:29 UTC
Update date2015-07-21 06:57:30 UTC
Primary IDFDB023087
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number25486-55-9
Structure
Thumb
Synonyms
SynonymSource
(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 oxideChEBI
Vitamin K1, epoxideChEBI
Phylloquinone 2,3-epoxideHMDB
Vitamin K epoxideHMDB
Vitamin K(1) oxideMeSH
Vitamin K1 epoxideMeSH
Vitamin K1 2,3-epoxideKEGG
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-Epoxyphylloquinonehmdb
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinonehmdb
Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-Phylloquinone oxidehmdb
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP8.28ALOGPS
logP9.22ChemAxon
logS-7.3ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC31H46O3
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
InChI IdentifierInChI=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
InChI KeyKUTXFBIHPWIDJQ-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O
Average Molecular Weight466.6951
Monoisotopic Molecular Weight466.344695338
Classification
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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w30-4954300000-8d5869c90a073d1fc4dbView in MoNA
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
ChemSpider ID4444391
ChEMBL IDCHEMBL299632
KEGG Compound IDC05849
Pubchem Compound ID5280845
Pubchem Substance IDNot Available
ChEBI ID28371
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02972
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Vitamin K epoxide reductase complex subunit 1VKORC1Q9BQB6
Pathways
NameSMPDB LinkKEGG Link
Vitamin K MetabolismSMP00464 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference