Showing metabocard for 13S-hydroxyoctadecadienoic acid (BMDB0004667)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:10:04 UTC
Update Date2020-05-11 20:40:56 UTC
BMDB IDBMDB0004667
Secondary Accession Numbers
  • BMDB04667
Metabolite Identification
Common Name13S-hydroxyoctadecadienoic acid
Description13-HODE, also known as 13(S) hode or (S)-coriolic 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. Thus, 13-HODE is considered to be an octadecanoid. Based on a literature review a significant number of articles have been published on 13-HODE.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13S)-Hydroxyoctadecadienoic acidChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(13S)-HydroxyoctadecadienoateGenerator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
13S-HydroxyoctadecadienoateHMDB
13-Hydroxy-9,11-octadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomerHMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomerHMDB
13-Hydroxyoctadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomerHMDB
13(S) HODEHMDB
13-HydroxyoctadecadienoateHMDB
(+)-Coriolic acidHMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acidHMDB
(S)-Coriolic acidHMDB
(±)-coriolic acidHMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acidHMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acidHMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acidHMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acidHMDB
13-Hydroxylinoleic acidHMDB
13-Hydroxyoctadeca-9,11-dienoic acidHMDB
13S-HODEHMDB
13S-Hydroxy-9Z,11E-octadecadienoic acidHMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acidHMDB
alpha-Artemisolic acidHMDB
Α-artemisolic acidHMDB
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoateHMDB
(9Z,11E)-13-HODEHMDB
(9Z,11E)-13-Hydroxyoctadecadienoic acidHMDB
FA(18:2(9Z,11E,13-OH))HMDB
FA(18:2(9Z,11E,13S-OH))HMDB
13-HODEHMDB, MeSH
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
Traditional Name13-hydroxyoctadecadienoic acid
CAS Registry Number5204-88-6
SMILES
CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
InChI KeyHNICUWMFWZBIFP-IRQZEAMPSA-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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
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 Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-054k-6960000000-8cc8c4da0c87c3d65f03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fbi-9342100000-19627880cd07ec05cb84View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3ff43b79ccb7acee5d87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1190000000-59a7f430444bdc36b530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2687cbf01f8a4a08925fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-fc43967f64934b080413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1490000000-d60f46720ed576787816View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9330000000-9622ef3fb83ca1fa8e96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-bed7738fb8e72e8df932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h7j-4490000000-e9f46847d2cc004e1b77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9520000000-57ec0699995e3751af99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-e3207ecec01bdd3e10e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ua-4930000000-a68be67edda5292d6ba1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9600000000-1e60462f1a3dff344af4View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004667
DrugBank IDDB06926
Phenol Explorer Compound IDNot Available
FooDB IDFDB112215
KNApSAcK IDC00000403
Chemspider ID4947055
KEGG Compound IDC14762
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link13-Hydroxyoctadecadienoic acid
METLIN IDNot Available
PubChem Compound6443013
PDB IDNot Available
ChEBI ID34154
References
Synthesis ReferenceBanks, A.; Keay, J. N.; Smith, J. G. M. Structure of conjugated methyl linoleate hydroperoxide. Nature (London, United Kingdom) (1957), 179 1078.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available