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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:54:59 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0010203
Secondary Accession Numbers
  • HMDB10203
Metabolite Identification
Common Name13-HOTE
Description13-HOTE 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. Thus, 13-HOTE is considered to be an octadecanoid. Based on a literature review a small amount of articles have been published on 13-HOTE.
Structure
Data?1582752796
Synonyms
ValueSource
13-Hydroxy-9Z,11E,15Z-octadecatrienoic acidChEBI
13-OH-9Z,11E,15Z-Octadecatrienoic acidChEBI
13-Hydroxy-9Z,11E,15Z-octadecatrienoateGenerator
13-OH-9Z,11E,15Z-OctadecatrienoateGenerator
13-Hydroxyoctadecatrienic acidMeSH
13-HOTEChEBI
Chemical FormulaC18H30O3
Average Molecular Weight294.429
Monoisotopic Molecular Weight294.219494826
IUPAC Name(9Z,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid
Traditional Name13-hote
CAS Registry NumberNot Available
SMILES
CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)/b9-7-,11-3-,15-12+
InChI KeyKLLGGGQNRTVBSU-JDTPQGGVSA-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 Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.006 g/LALOGPS
logP5.39ALOGPS
logP4.83ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
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
Polarizability36.38 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]+178.89931661259
DarkChem[M-H]-178.53631661259
DeepCCS[M+H]+177.97630932474
DeepCCS[M-H]-175.61830932474
DeepCCS[M-2H]-208.50530932474
DeepCCS[M+Na]+184.0730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13-HOTECC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O3911.9Standard polar33892256
13-HOTECC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O2291.0Standard non polar33892256
13-HOTECC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O2397.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13-HOTE,1TMS,isomer #1CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2561.3Semi standard non polar33892256
13-HOTE,1TMS,isomer #2CC/C=C\CC(O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2473.9Semi standard non polar33892256
13-HOTE,2TMS,isomer #1CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2534.6Semi standard non polar33892256
13-HOTE,1TBDMS,isomer #1CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2804.2Semi standard non polar33892256
13-HOTE,1TBDMS,isomer #2CC/C=C\CC(O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2716.8Semi standard non polar33892256
13-HOTE,2TBDMS,isomer #1CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3023.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13-HOTE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-9660000000-cdd31a587f020c6bb71f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-HOTE GC-MS (2 TMS) - 70eV, Positivesplash10-0109-9544200000-b0a869f13b7e4fa483382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-HOTE 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 - 13-HOTE 10V, Positive-QTOFsplash10-004i-0090000000-746f819f93600145d24c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 20V, Positive-QTOFsplash10-05r1-3590000000-b132154678fe02b12c682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 40V, Positive-QTOFsplash10-00kr-9620000000-83daf6b2d2d82029206d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 10V, Negative-QTOFsplash10-0006-0090000000-901bbdc98a5faa93989d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 20V, Negative-QTOFsplash10-004l-1090000000-ef28369e562e3118852d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 40V, Negative-QTOFsplash10-0a4l-9220000000-ce8f9d891009dab59be92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 10V, Positive-QTOFsplash10-004i-0590000000-bb484c38b00b61a4c5c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 20V, Positive-QTOFsplash10-0561-3920000000-0a0eff6d89655b3e7e3a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 40V, Positive-QTOFsplash10-067i-9700000000-dd60260108f968b4a1532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 10V, Negative-QTOFsplash10-002f-0090000000-e447b375f3a269ef29762021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 20V, Negative-QTOFsplash10-004l-1390000000-d48b71d8fb0d418ae2de2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-HOTE 40V, Negative-QTOFsplash10-0006-9310000000-070b30fb068bd05ccdb92021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000493 +/- 0.000017 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00190 +/- 0.000207 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.0019 +/- 0.00021 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00111 +/- 0.00074 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027358
KNApSAcK IDNot Available
Chemspider ID8645139
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10469728
PDB IDNot Available
ChEBI ID72641
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. Collins JF, Hu Z, Ranganathan PN, Feng D, Garrick LM, Garrick MD, Browne RW: Induction of arachidonate 12-lipoxygenase (Alox15) in intestine of iron-deficient rats correlates with the production of biologically active lipid mediators. Am J Physiol Gastrointest Liver Physiol. 2008 Apr;294(4):G948-62. doi: 10.1152/ajpgi.00274.2007. Epub 2008 Feb 7. [PubMed:18258795 ]