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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:46:38 UTC
Update Date2022-03-07 02:53:10 UTC
HMDB IDHMDB0031934
Secondary Accession Numbers
  • HMDB31934
Metabolite Identification
Common Name(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
Description(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review very few articles have been published on (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid.
Structure
Data?1563862194
Synonyms
ValueSource
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoateGenerator
4-Acetylpiperidinium chlorideHMDB
9-Hydroxy-(S-(e,Z,Z))-10-12-15-octadecatrienoic acidHMDB
9-Hydroxy-10,12,15-octadecatrienoic acidHMDB
(10E,12E,15E)-9-Hydroxyoctadeca-10,12,15-trienoateGenerator
9-OH-10,12,15-ODTAMeSH
(10E,12Z,15Z)-9-OH-10,12,15-ODTAMeSH
Chemical FormulaC18H30O3
Average Molecular Weight294.429
Monoisotopic Molecular Weight294.219494826
IUPAC Name(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoic acid
Traditional Name(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoic acid
CAS Registry Number89886-42-0
SMILES
CC\C=C\C\C=C\C=C\C(O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3+,8-6+,14-11+
InChI KeyRIGGEAZDTKMXSI-JPAZTHTMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
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 Solubility0.0073 g/LALOGPS
logP5.31ALOGPS
logP4.83ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity91.15 m³·mol⁻¹ChemAxon
Polarizability37.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.70431661259
DarkChem[M-H]-179.02931661259
DeepCCS[M+H]+175.30130932474
DeepCCS[M-H]-172.94330932474
DeepCCS[M-2H]-205.82930932474
DeepCCS[M+Na]+181.39430932474
AllCCS[M+H]+179.432859911
AllCCS[M+H-H2O]+176.332859911
AllCCS[M+NH4]+182.232859911
AllCCS[M+Na]+183.032859911
AllCCS[M-H]-178.732859911
AllCCS[M+Na-2H]-180.232859911
AllCCS[M+HCOO]-181.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acidCC\C=C\C\C=C\C=C\C(O)CCCCCCCC(O)=O3929.5Standard polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acidCC\C=C\C\C=C\C=C\C(O)CCCCCCCC(O)=O2284.7Standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acidCC\C=C\C\C=C\C=C\C(O)CCCCCCCC(O)=O2402.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,1TMS,isomer #1CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O)O[Si](C)(C)C2554.7Semi standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,1TMS,isomer #2CC/C=C/C/C=C/C=C/C(O)CCCCCCCC(=O)O[Si](C)(C)C2471.4Semi standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,2TMS,isomer #1CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2526.0Semi standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,1TBDMS,isomer #1CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2797.4Semi standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,1TBDMS,isomer #2CC/C=C/C/C=C/C=C/C(O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2711.4Semi standard non polar33892256
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid,2TBDMS,isomer #1CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3011.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi3-3950000000-8a156f6aacc3fef03a472017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9343200000-d39c3c3fa524d4ba3dc12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic 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 - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 10V, Positive-QTOFsplash10-004j-0090000000-45743ea560c95e3a11312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 20V, Positive-QTOFsplash10-0561-5590000000-cc5903987b827d8d76072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 40V, Positive-QTOFsplash10-05nf-9210000000-1d1303757febc46ca7ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 10V, Negative-QTOFsplash10-0006-0090000000-feac899c3e186bbd60482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 20V, Negative-QTOFsplash10-0006-1290000000-439494f75889afaaf9e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 40V, Negative-QTOFsplash10-0a4i-9620000000-49b04b57fed59d39db112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 10V, Negative-QTOFsplash10-0006-0090000000-c394151db56c45114e152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 20V, Negative-QTOFsplash10-002f-0290000000-3a5292edaff278d3011a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 40V, Negative-QTOFsplash10-0a6u-8940000000-2becc40f3081dee12c5b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 10V, Positive-QTOFsplash10-056r-1390000000-c0970460d0fcd9445fb12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 20V, Positive-QTOFsplash10-053r-6920000000-795d5ec054d8e50ac7362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid 40V, Positive-QTOFsplash10-05ru-9200000000-cec78684db63d3cd17412021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000503 +/- 0.000052 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 IDFDB008622
KNApSAcK IDC00048303
Chemspider ID20144227
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13917187
PDB IDNot Available
ChEBI ID89388
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .