Showing metabocard for Vitamin K1 2,3-epoxide (BMDB0002972)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:02:18 UTC
Update Date2020-04-22 15:11:34 UTC
BMDB IDBMDB0002972
Secondary Accession Numbers
  • BMDB02972
Metabolite Identification
Common NameVitamin K1 2,3-epoxide
DescriptionVitamin K1 2,3-epoxide, also known as phylloquinone epoxide or vitamin K1 oxide, 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. Vitamin K1 2,3-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2,3-Epoxyphytyl)menaquinoneKegg
2,3-Epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinoneKegg
2,3-EpoxyphylloquinoneKegg
1a,7a-Dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dioneKegg
Phylloquinone oxideKegg
Phylloquinone epoxideKegg
Phylloquinone-2,3-epoxideKegg
Vitamin K1 oxideKegg
Vitamin K(1) oxideMeSH
Vitamin K1 epoxideMeSH
Vitamin K epoxideMeSH
Vitamin K1 2,3-epoxideKEGG
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinoneChEBI, HMDB
Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxideChEBI, HMDB
Phylloquinone, epoxideChEBI, HMDB
Vitamin K 2,3-epoxideChEBI, HMDB
Vitamin K1, epoxideChEBI, HMDB
Phylloquinone 2,3-epoxideHMDB
Chemical FormulaC31H46O3
Average Molecular Weight466.706
Monoisotopic Molecular Weight466.344695341
IUPAC Name1a-methyl-7a-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione
Traditional Name1a-methyl-7a-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphtho[2,3-b]oxirene-2,7-dione
CAS Registry Number25486-55-9
SMILES
CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC12OC1(C)C(=O)C1=C(C=CC=C1)C2=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 KeyKUTXFBIHPWIDJQ-LKUDQCMESA-N
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
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability56.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gx0-6977600000-2137df8652a4638c24c0View 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-4590300000-2c3880d696065a134cffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9880100000-8ee08aa2babfb4cf02f5View 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
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0062451
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280845
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Vitamin K epoxide reductase complex subunit 1
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. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development (By similarity).
Gene Name:
VKORC1
Uniprot ID:
Q6B4J2
Molecular weight:
17967.0