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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-18 11:41:18 UTC
Update Date2022-03-07 02:49:25 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
Data?1582752342
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-Hydroxy-(8Z,11Z,13E)-eicosatrienoateGenerator
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoateGenerator
15-HydroxyeicosatrienoateGenerator
15S-Hydroxy-8Z,11Z,13E-eicosatrienoateGenerator
15(S)-HydroxyeicosatrienoateGenerator
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
Description 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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0009 g/LALOGPS
logP6.2ALOGPS
logP5.72ChemAxon
logS-5.6ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.4531661259
DarkChem[M-H]-190.45131661259
DeepCCS[M+H]+189.90930932474
DeepCCS[M-H]-187.55130932474
DeepCCS[M-2H]-220.43730932474
DeepCCS[M+Na]+196.00230932474
AllCCS[M+H]+188.432859911
AllCCS[M+H-H2O]+185.532859911
AllCCS[M+NH4]+191.032859911
AllCCS[M+Na]+191.732859911
AllCCS[M-H]-187.032859911
AllCCS[M+Na-2H]-188.932859911
AllCCS[M+HCOO]-191.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15(S)-Hydroxyeicosatrienoic acidCCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O4108.6Standard polar33892256
15(S)-Hydroxyeicosatrienoic acidCCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O2432.0Standard non polar33892256
15(S)-Hydroxyeicosatrienoic acidCCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O2604.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15(S)-Hydroxyeicosatrienoic acid,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C2730.3Semi standard non polar33892256
15(S)-Hydroxyeicosatrienoic acid,1TMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C2646.7Semi standard non polar33892256
15(S)-Hydroxyeicosatrienoic acid,2TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2717.3Semi standard non polar33892256
15(S)-Hydroxyeicosatrienoic acid,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2979.9Semi standard non polar33892256
15(S)-Hydroxyeicosatrienoic acid,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C2889.0Semi standard non polar33892256
15(S)-Hydroxyeicosatrienoic acid,2TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3218.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-6592000000-9dc0f3f0bbc2de8a434d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9332200000-cf5f429c3867c843e3f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Positive-QTOFsplash10-0a4i-0059000000-a80d73087c4ff885f7622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Positive-QTOFsplash10-0a4i-4393000000-64b119d876007616dced2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Positive-QTOFsplash10-03kc-9630000000-2bff72917aba29b0568d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Negative-QTOFsplash10-00di-0019000000-4c24ada22b9690dcb2fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Negative-QTOFsplash10-0fk9-2059000000-6a462b1cbfb1f2633ec22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Negative-QTOFsplash10-0a4l-9130000000-973ff7b5957c59e993272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Negative-QTOFsplash10-0fk9-0009000000-57568fa8a4085a5e528c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Negative-QTOFsplash10-0uk9-1249000000-c0ee7a1e26de1f84a01c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Negative-QTOFsplash10-0006-9140000000-a469f1131b8f8929c25e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Positive-QTOFsplash10-0a4i-0459000000-12a2a03e81c41e9d9b572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Positive-QTOFsplash10-052r-1953000000-ce7b9656736b3429c15a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Positive-QTOFsplash10-067i-9600000000-dee10fd76962f5b5aae82021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 +/- 0.000015 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023608
KNApSAcK IDC00000182
Chemspider ID4446269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283145
PDB IDNot Available
ChEBI ID88348
Food Biomarker OntologyNot Available
VMH IDCE2537
MarkerDB IDNot Available
Good Scents IDrw1797471
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 ]