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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-14 01:21:57 UTC
Update Date2020-02-26 21:25:13 UTC
HMDB IDHMDB0004702
Secondary Accession Numbers
  • HMDB04702
Metabolite Identification
Common Name12,13-EpOME
Description12,13-EpOME, also known as vernolsaeure or vernolic acids, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 12,13-epome is considered to be an octadecanoid lipid molecule. 12,13-EpOME is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752313
Synonyms
ValueSource
(9Z)-11-(3-Pentyloxiran-2-yl)undec-9-enoic acidsChEBI
(9Z)-12,13-Epoxyoctadecenoic acidChEBI
12(13)-EpOMEChEBI
12,13-cis-Epoxyoctadecenoic acidChEBI
12,13-Epoxy-9(Z)-octadecenoic acidChEBI
12,13-Epoxy-cis-9-octadecenoic acidChEBI
12,13-Monoepoxy-cis-9-octadecenoic acidChEBI
Acide vernoliqueChEBI
cis-12,13-Ep, 9C-18:1ChEBI
cis-12,13-Epoxy-9-octadecenoic acidChEBI
Vernolic acidsChEBI
VernolsaeureChEBI
VernolsaeurenChEBI
(9Z)-12,13-EpoxyoctadecenoateGenerator
12,13-cis-EpoxyoctadecenoateGenerator
12,13-Epoxy-9(Z)-octadecenoateGenerator
12,13-Epoxy-cis-9-octadecenoateGenerator
12,13-Monoepoxy-cis-9-octadecenoateGenerator
cis-12,13-Epoxy-9-octadecenoateGenerator
(+/-)-12(13)-epoxy-9Z-octadecenoateHMDB
(+/-)-12(13)-epoxy-9Z-octadecenoic acidHMDB
(9Z)-11-(3-Pentyloxiran-2-yl)undec-9-enoateHMDB
(9Z)-11-(3-Pentyloxiran-2-yl)undec-9-enoic acidHMDB
12,13-Epoxyoctadec-9(Z)-enoateHMDB
12,13-Epoxyoctadec-9(Z)-enoic acidHMDB
Vernolic acidHMDB
cis-12-Epoxyoctadeca-cis-9-enoateHMDB
cis-12-Epoxyoctadeca-cis-9-enoic acidHMDB
VernoleateHMDB
12,13-EOAHMDB
12,13-Epoxy-9-octadecenoic acidHMDB
VernolateGenerator
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid
Traditional 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
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00048 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 Area49.83 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity86.92 m³·mol⁻¹ChemAxon
Polarizability37.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ng-8950000000-c5cd8bcc7660edd193bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0abi-9461000000-ee542501a93901368313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-bdb34bd2906b9903a919Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00a9-9850000000-f325928e52a1c0523bd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9400000000-73273401d57d3e2d0464Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-a3e75e0d5c18ce62d0ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2190000000-783d4add45a350928417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-ffe7b3e31523bb0ac1b4Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00725 +/- 0.00673 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00488 +/- 0.00034 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00721 +/- 0.0088 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00139 +/- 0.00109 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023414
KNApSAcK IDNot Available
Chemspider ID4512106
KEGG Compound IDC14826
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5356421
PDB IDNot Available
ChEBI ID38299
Food Biomarker OntologyNot Available
VMH IDC14826
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 24 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81

Only showing the first 10 proteins. There are 24 proteins in total.