Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:29:16 UTC
Update Date2021-10-01 18:49:22 UTC
HMDB IDHMDB0245416
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Epoxyphylloquinone
Description2,3-Epoxyphylloquinone, also known as phylloquinone epoxide or vitamin K 2,3-epoxide, 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. Based on a literature review very few articles have been published on 2,3-Epoxyphylloquinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3-epoxyphylloquinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3-Epoxyphylloquinone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
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
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
Vitamin K epoxideHMDB
Vitamin K(1) oxideHMDB
Vitamin K1 epoxideHMDB
Phylloquinone 2,3-epoxideHMDB
2,3-EpoxyphylloquinoneChEBI
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 NumberNot Available
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
InChI KeyKUTXFBIHPWIDJQ-UHFFFAOYSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability57.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+221.332859911
AllCCS[M+H-H2O]+219.632859911
AllCCS[M+NH4]+222.932859911
AllCCS[M+Na]+223.432859911
AllCCS[M-H]-218.032859911
AllCCS[M+Na-2H]-221.032859911
AllCCS[M+HCOO]-224.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-EpoxyphylloquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O4209.8Standard polar33892256
2,3-EpoxyphylloquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O3259.1Standard non polar33892256
2,3-EpoxyphylloquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O3324.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin-K-epoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w30-4954300000-8d5869c90a073d1fc4db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin-K-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 - 2,3-Epoxyphylloquinone 10V, Positive-QTOFsplash10-014i-0130900000-3b1bc358b43e27854bb62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 20V, Positive-QTOFsplash10-0ktk-5690300000-ece538d0d9bd3857484a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 40V, Positive-QTOFsplash10-0a4i-9880100000-4aeb98e31bc2eec7a7cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 10V, Negative-QTOFsplash10-014i-0000900000-d7ac14f3da074ab1a0a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 20V, Negative-QTOFsplash10-014i-0010900000-f6d434f05e8f2c7c56db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 40V, Negative-QTOFsplash10-0udi-6891300000-6a0524a63604098eb1bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 10V, Positive-QTOFsplash10-014i-0011900000-5903a04b878c5d82fdbd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 20V, Positive-QTOFsplash10-0bu1-9630200000-9504569510e38183ff132021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 40V, Positive-QTOFsplash10-0002-9611000000-282beae1fca6c1b31a2b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 10V, Negative-QTOFsplash10-014i-0000900000-34d4a26fdf7a1cd267302021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 20V, Negative-QTOFsplash10-014r-0300900000-b1c60108747d75cb70952021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyphylloquinone 40V, Negative-QTOFsplash10-004r-0209100000-3de9eac366ee0b0673ca2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 ID82688
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91577
PDB IDNot Available
ChEBI ID28371
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1770491
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

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
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
General function:
Not Available
Specific function:
Not Available
Gene Name:
VKORC1L1
Uniprot ID:
Q8N0U8
Molecular weight:
19835.4
General function:
Not Available
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:
Q07175
Molecular weight:
87556.395