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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-14 01:03:56 UTC
Update Date2018-05-19 22:24:56 UTC
HMDB IDHMDB0004701
Secondary Accession Numbers
  • HMDB04701
Metabolite Identification
Common Name9,10-Epoxyoctadecenoic acid
Description9,10-Epoxyoctadecenoic acid (9,10-EOA) is a peroxidation product of linoleic acid (LA). 9,10-EOA is a naturally occurring component of oxidized low density lipoprotein (LDL), the level of which increases with aging, atherosclerosis, and rheumatoid arthritis, perhaps due to an increase in 15-lipoxygenase and free oxygen radicals. 9,10-EOA is a proliferator-activated receptors (PPAR) gamma2 ligand, that is antiosteogenic without stimulating adipocyte differentiation. Studies in dogs suggest that 9,10-EOA has toxic cardiovascular effects. (PMID: 12665667 , 12021203 , 10667371 ).
Structure
Thumb
Synonyms
ValueSource
9(10)-Epoxyoctadec-12Z-enoic acidChEBI
9,10-EOAChEBI
9,10-Epoxy-12Z-octadecenoic acidChEBI
9,10-Epoxyoctadec-12(Z)-enoic acidChEBI
Coronaric acidChEBI
9(10)-Epoxyoctadec-12Z-enoateGenerator
9,10-EpoxyoctadecenoateGenerator
9,10-Epoxy-12Z-octadecenoateGenerator
9,10-Epoxyoctadec-12(Z)-enoateGenerator
CoronarateGenerator
(+/-)-9(10)-epoxy-12Z-octadecenoateHMDB
(+/-)-9(10)-epoxy-12Z-octadecenoic acidHMDB
9(10)-EpOMEHMDB
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid
Traditional Name9,10-epoxyoctadecenoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/CC1OC1CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b10-7-
InChI KeyFBUKMFOXMZRGRB-YFHOEESVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.0005 g/LALOGPS
logP6.35ALOGPS
logP5.48ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
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
Polarizability37.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0596-7950000000-a7d6f240b5040a8c27a7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0h99-9752000000-4d63c881504328381437View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-8fcb6e52fa137a01bdb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-020r-6940000000-aed267f1e6e4cb3f5209View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9200000000-3e01c026dad4bd3c61a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-60908406af279bf8075cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-1390000000-3d68f1fc729ac1835d04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9800000000-847443fa21f1bd143f61View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00150 +/- 0.000974 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00217 +/- 0.00023 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00547 +/- 0.0074 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00151 +/- 0.00121 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
FoodDB IDFDB003107
KNApSAcK IDNot Available
Chemspider ID4861048
KEGG Compound IDC14825
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6246154
PDB IDNot Available
ChEBI ID34494
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mitchell LA, Grant DF, Melchert RB, Petty NM, Kennedy RH: Linoleic acid metabolites act to increase contractility in isolated rat heart. Cardiovasc Toxicol. 2002;2(3):219-30. [PubMed:12665667 ]
  2. Lecka-Czernik B, Moerman EJ, Grant DF, Lehmann JM, Manolagas SC, Jilka RL: Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation. Endocrinology. 2002 Jun;143(6):2376-84. [PubMed:12021203 ]
  3. Jira W, Spiteller G: Dramatic increase of linoleic acid peroxidation products by aging, atherosclerosis, and rheumatoid arthritis. Adv Exp Med Biol. 1999;469:479-83. [PubMed:10667371 ]

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.