Record Information
Version3.6
Creation Date2006-08-14 01:21:57 UTC
Update Date2013-02-09 00:13:20 UTC
HMDB IDHMDB04702
Secondary Accession NumbersNone
Metabolite Identification
Common Name12,13-EpOME
Description12,13-EpOME is the 12,13-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. The toxicity and biosynthesis of 12,13-EpOME has not been well differentiated from 9,10-EpOME, but has been presumed to be essentially the same.P.
Structure
Thumb
Synonyms
  1. (+/-)-12(13)-epoxy-9Z-octadecenoate
  2. (+/-)-12(13)-epoxy-9Z-octadecenoic acid
  3. (9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoate
  4. (9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid
  5. (9Z)-12,13-epoxyoctadecenoate
  6. (9Z)-12,13-epoxyoctadecenoic acid
  7. 12(13)-EpOME
  8. 12,13-Epoxy-9(Z)-octadecenoate
  9. 12,13-Epoxy-9(Z)-octadecenoic acid
  10. 12,13-Epoxyoctadec-9(Z)-enoate
  11. 12,13-Epoxyoctadec-9(Z)-enoic acid
  12. Vernolic acid
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid
Traditional IUPAC Namevernolic acid
CAS Registry NumberNot Available
SMILES
CCCCCC1OC1C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-
InChI KeyCCPPLLJZDQAOHD-FLIBITNWSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassHeterocyclic Fatty Acids
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
Direct ParentEpoxy Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility4.780E-04 g/LALOGPS
logP6.37ALOGPS
logP5.48ChemAxon
logS-5.8ALOGPS
pKa (strongest acidic)4.99ChemAxon
pKa (strongest basic)-4.2ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area49.83ChemAxon
rotatable bond count14ChemAxon
refractivity86.92ChemAxon
polarizability37.2ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00725 +/- 0.00673 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified4.88 +/- 0.34 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified7.21 +/- 8.8 uMAdult (>18 years old)Not SpecifiedCommentNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.00139 +/- 0.00109 uMAdult (>18 years old)BothCommentNormal
  • John W. Newm...
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 IDFDB023414
KNApSAcK IDNot Available
Chemspider ID4512106
KEGG Compound IDC14826
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04702
Metagene LinkHMDB04702
METLIN IDNot Available
PubChem Compound5356421
PDB IDNot Available
ChEBI ID38299
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2C18
Uniprot ID:
P33260
Gene Name:
CYP2F1
Uniprot ID:
P24903
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP4B1
Uniprot ID:
P13584
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP19A1
Uniprot ID:
P11511
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Gene Name:
CYP2J2
Uniprot ID:
P51589
Gene Name:
CYP2A7
Uniprot ID:
P20853
Gene Name:
CYP2A6
Uniprot ID:
P11509
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0