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Record Information
Version4.0
Creation Date2008-09-15 09:54:59 UTC
Update Date2017-09-27 08:26:09 UTC
HMDB IDHMDB0010203
Secondary Accession Numbers
  • HMDB10203
Metabolite Identification
Common Name13-HOTE
Description13-HOTE is a biologically active lipid molecule produced due to altered intestinal lipid metabolism indicative of Alox15 activity. (PMID: 18258795 ).
Structure
Thumb
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
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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 Solubility0.006 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
Bioavailability1ChemAxon
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, Positivesplash10-00mo-9660000000-cdd31a587f020c6bb71fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0109-9544200000-b0a869f13b7e4fa48338View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-746f819f93600145d24cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-3590000000-b132154678fe02b12c68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9620000000-83daf6b2d2d82029206dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-901bbdc98a5faa93989dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-1090000000-ef28369e562e3118852dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9220000000-ce8f9d891009dab59be9View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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 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
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 ]