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Record Information
Version3.6
Creation Date2006-08-14 02:27:54 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04710
Secondary Accession NumbersNone
Metabolite Identification
Common Name9,10,13-TriHOME
Description9,10,13-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.
Structure
Thumb
Synonyms
ValueSource
(11E)-9,10,13-Trihydroxyoctadec-11-enoateHMDB
(11E)-9,10,13-Trihydroxyoctadec-11-enoic acidHMDB
(e)-9,10,13-Trihydroxy-11-octadecenoateHMDB
(e)-9,10,13-Trihydroxy-11-octadecenoic acidHMDB
9,10,13-Trihydroxy-11-octadecenoateHMDB
9,10,13-Trihydroxy-11-octadecenoic acidHMDB
9,10,13-Trihydroxyoctadec-11-enoateHMDB
9,10,13-Trihydroxyoctadec-11-enoic acidHMDB
Chemical FormulaC18H34O5
Average Molecular Weight330.4596
Monoisotopic Molecular Weight330.240624198
IUPAC Name(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid
Traditional Name(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid
CAS Registry Number29907-57-1
SMILES
CCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O5/c1-2-3-7-10-15(19)13-14-17(21)16(20)11-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17+/m0/s1
InChI KeyInChIKey=NTVFQBIHLSPEGQ-SYMVGPSASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility0.15 mg/mLALOGPS
logP3.76ALOGPS
logP3.25ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.79 m3·mol-1ChemAxon
Polarizability39.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000513 +/- 0.000083 (0.000430 - 0.000596) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000513 +/- 0.000083 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00116 +/- 0.00064 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00033 +/- 0.00018 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023419
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14835
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04710
Metagene LinkHMDB04710
METLIN IDNot Available
PubChem Compound14968868
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available