Showing metabocard for 9-HODE (BMDB0010223)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:01:41 UTC
Update Date2020-04-22 15:39:31 UTC
BMDB IDBMDB0010223
Secondary Accession Numbers
  • BMDB10223
Metabolite Identification
Common Name9-HODE
Description9-HODE 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, 9-HODE is considered to be an octadecanoid lipid molecule. 9-HODE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-Hydroxy-10,12-octadecadienoateHMDB
9-Hydroxy-10,12-octadecadienoic acidHMDB
9-Hydroxy-10E,12E-octadecadienoateHMDB
9-Hydroxy-10E,12E-octadecadienoic acidHMDB
9-Hydroxy-trans-10,trans-12-octadecadienoateHMDB
9-Hydroxy-trans-10,trans-12-octadecadienoic acidHMDB
9-Hydroxylinoleic acidHMDB
alpha-Dimorphecolic acidHMDB
Dimorphecolic acidHMDB
9-OH-18:2DElta(10t,12t)HMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomerHMDB
DimorphecolateGenerator
9-HODEMeSH
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(10E,12E)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Namedimorphecolic acid
CAS Registry Number15514-85-9
SMILES
CCCCC\C=C\C=C\C(O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+
InChI KeyNPDSHTNEKLQQIJ-SIGMCMEVSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
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)4.68ChemAxon
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
Polarizability37.98 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, Positivesplash10-0uml-6950000000-9a2499db5f3aa8592e67View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9133100000-615fce6d28e837fb087eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-003v-9500000000-d29ea1ddd6c443a677efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-cb7f83c104f8b4f7a5d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ur-5590000000-52b5fc3231b31e1bdbcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9210000000-ecf9bc7db0c47c498040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3d5630b842dbad3bc887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0190000000-9af33ffd09081fae6778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9720000000-fc7436feeb97b5db2c89View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010223
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031387
KNApSAcK IDNot Available
Chemspider ID4446072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link9-Hydroxyoctadecadienoic acid
METLIN IDNot Available
PubChem Compound5282945
PDB IDNot Available
ChEBI ID595882
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available