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Record Information
Version3.6
Creation Date2006-10-18 11:41:18 UTC
Update Date2016-02-11 01:07:03 UTC
HMDB IDHMDB05045
Secondary Accession NumbersNone
Metabolite Identification
Common Name15(S)-Hydroxyeicosatrienoic acid
Description15(S)-hydroxyeicosatrienoic acid (15S-HETrE) is the in vivo metabolite of gamma-linolenic acid, a polyunsaturated fatty acid that have been reported to modulate arachidonic acid (AA) metabolism and tumorigenesis. 15S-HETrE suppress cyclooxygenase-2 (COX-2) over expression and/or Prostaglandin E2 (PGE2) biosynthesis (PMID 15197770 ), and inhibits [(3)H]thymidine uptake in parallel with the upregulation of peroxisome proliferator-activated receptor-gamma expression (a growth modulating nuclear receptor, PPARgamma). (PMID 12445673 ).
Structure
Thumb
Synonyms
ValueSource
15(S)-HydroxyeicosatrienoateHMDB
15-HETrEHMDB
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoateHMDB
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoic acidHMDB
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoateHMDB
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoic acidHMDB
15-HydroxyeicosatrienoateHMDB
15-Hydroxyeicosatrienoic acidHMDB
15S-HETrEHMDB
15S-Hydroxy-8Z,11Z,13E-eicosatrienoateHMDB
15S-Hydroxy-8Z,11Z,13E-eicosatrienoic acidHMDB
Chemical FormulaC20H34O3
Average Molecular Weight322.4822
Monoisotopic Molecular Weight322.250794954
IUPAC Name(8Z,11Z,13E,15S)-15-hydroxyicosa-8,11,13-trienoic acid
Traditional Name6-deoxy-L-sorbose
CAS Registry Number13-16-1
SMILES
CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,11-9-,17-14+/t19-/m0/s1
InChI KeyInChIKey=IUKXMNDGTWTNTP-OAHXIXLCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 (predicted from logP)
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 Solubility0.000902 mg/mLALOGPS
logP6.2ALOGPS
logP5.72ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.35 m3·mol-1ChemAxon
Polarizability39.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000253 +/- 0.000018 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000437 +/- 0.000028 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000732 +/- 0.00045 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000421 +/- 1.5E-5 uMAdult (>18 years old)BothNormal 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 IDFDB023608
KNApSAcK IDNot Available
Chemspider ID4446269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05045
Metagene LinkHMDB05045
METLIN IDNot Available
PubChem Compound5283145
PDB IDNot Available
ChEBI ID17897
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pham H, Banerjee T, Ziboh VA: Suppression of cyclooxygenase-2 overexpression by 15S-hydroxyeicosatrienoic acid in androgen-dependent prostatic adenocarcinoma cells. Int J Cancer. 2004 Aug 20;111(2):192-7. [15197770 ]
  2. Pham H, Banerjee T, Nalbandian GM, Ziboh VA: Activation of peroxisome proliferator-activated receptor (PPAR)-gamma by 15S-hydroxyeicosatrienoic acid parallels growth suppression of androgen-dependent prostatic adenocarcinoma cells. Cancer Lett. 2003 Jan 10;189(1):17-25. [12445673 ]