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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-18 11:41:18 UTC
Update Date2017-10-23 19:04:15 UTC
HMDB IDHMDB0005045
Secondary Accession Numbers
  • HMDB05045
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
(8Z,11Z,13E,15S)-15-Hydroxyicosatrienoic acidChEBI
15-HETrEChEBI
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoic acidChEBI
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoic acidChEBI
15-Hydroxyeicosatrienoic acidChEBI
15S-HETrEChEBI
15S-Hydroxy-8Z,11Z,13E-eicosatrienoic acidChEBI
(8Z,11Z,13E,15S)-15-HydroxyicosatrienoateGenerator
15(S)-HydroxyeicosatrienoateGenerator
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoateGenerator
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoateGenerator
15-HydroxyeicosatrienoateGenerator
15S-Hydroxy-8Z,11Z,13E-eicosatrienoateGenerator
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 KeyIUKXMNDGTWTNTP-OAHXIXLCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.0009 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.35 m³·mol⁻¹ChemAxon
Polarizability39.47 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0pi0-6592000000-9dc0f3f0bbc2de8a434dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9332200000-cf5f429c3867c843e3f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0059000000-a80d73087c4ff885f762View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4393000000-64b119d876007616dcedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kc-9630000000-2bff72917aba29b0568dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-4c24ada22b9690dcb2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-2059000000-6a462b1cbfb1f2633ec2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-973ff7b5957c59e99327View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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. [PubMed: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. [PubMed:12445673 ]