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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-14 02:16:26 UTC
Update Date2018-05-19 22:25:00 UTC
HMDB IDHMDB0004708
Secondary Accession Numbers
  • HMDB04708
Metabolite Identification
Common Name9,12,13-TriHOME
Description9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883 , 6414520 ).
Structure
Thumb
Synonyms
ValueSource
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acidChEBI
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoic acidChEBI
9S,12S,13S-Trihydroxy-10E-octadecenoic acidChEBI
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoateGenerator
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoateGenerator
9S,12S,13S-Trihydroxy-10E-octadecenoateGenerator
Chemical FormulaC18H34O5
Average Molecular Weight330.4596
Monoisotopic Molecular Weight330.240624198
IUPAC Name(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid
Traditional Name(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1
InChI KeyMDIUMSLCYIJBQC-MVFSOIOZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility0.16 g/LALOGPS
logP3.77ALOGPS
logP3.25ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.79 m³·mol⁻¹ChemAxon
Polarizability40.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-01t9-8793000000-4ec3797bc6aecb279c19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ufs-8320956000-3d261be1a62b70fb10fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0169000000-4922950b9eca14aa8455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yj-6952000000-20e6d96b68b41142b124View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rx-9410000000-9cfd45c735431ceee09fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-5b501130985f198d7943View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4898000000-4a8ad508f3317957828cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9530000000-1cce1c79d4d82230a45fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000827 +/- 0.000214 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.000827 +/- 0.00021 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00411 +/- 0.0022 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023418
KNApSAcK IDNot Available
Chemspider ID8034429
KEGG Compound IDC14833
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9858729
PDB IDNot Available
ChEBI ID34506
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Funk CD, Powell WS: Release of prostaglandins and monohydroxy and trihydroxy metabolites of linoleic and arachidonic acids by adult and fetal aortae and ductus arteriosus. J Biol Chem. 1985 Jun 25;260(12):7481-8. [PubMed:3997883 ]
  2. Funk CD, Powell WS: Metabolism of linoleic acid by prostaglandin endoperoxide synthase from adult and fetal blood vessels. Biochim Biophys Acta. 1983 Nov 1;754(1):57-71. [PubMed:6414520 ]