Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 05:21:54 UTC
Update Date2022-03-07 03:17:57 UTC
HMDB IDHMDB0062652
Secondary Accession Numbers
  • HMDB62652
Metabolite Identification
Common Name(10E,12Z)-9-HODE
Description(10E,12Z)-9-HODE, also known as 9-Hydroxy-10E,12Z-octadecadienoic acid or 9-Hydroxylinoleic acid, is classified as a lineolic acid or a Lineolic acid derivative. Lineolic acids 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. (10E,12Z)-9-HODE is considered to be practically insoluble (in water) and acidic. (10E,12Z)-9-HODE is an octadecanoid lipid molecule
Structure
Data?1563866342
Synonyms
ValueSource
(10E,12Z)-9-HODEChEBI
9-Hydroxy-10E,12Z-octadecadienoic acidChEBI
9-Hydroxy-trans-10,cis-12-octadecadienoic acidChEBI
9-Hydroxy-10E,12Z-octadecadienoateGenerator
9-Hydroxy-trans-10,cis-12-octadecadienoateGenerator
9-Hydroxylinoleic acidMeSH
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomerMeSH
Dimorphecolic acidMeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomerMeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomerMeSH
9-OH-18:2DElta(10t,12t)MeSH
9-Hydroxy-10,12-octadecadienoic acidMeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomerMeSH
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomerMeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomerMeSH
(10E,​12Z)​-​9-​hydroxy-​10,​12-​octadecadienoic acidSMPDB, HMDB
9-​hydroxy-​10E,​12Z​-​octadecadienoic acidSMPDB, HMDB, ChEBI
9-​hydroxy-​(10E,​12Z)​-​octadeca-​10,​12-​dienoic acidSMPDB, HMDB
9-​hydroxy-​10(E)​,​12(Z)​-​octadecadienoic acidSMPDB, HMDB
9-​hydroxy-​10-​trans-12-​cis-​octadecadienoic acidSMPDB, HMDB
9-​hydroxy-​trans-10-cis-12-​​octadecadienoic acidSMPDB, HMDB
9-​hydroxyoctadeca-​10,​12​-​dienoic acidSMPDB, HMDB
9-​(E,​Z)​-​HODESMPDB, HMDB
9-HODESMPDB, HMDB
9-​hydroxylinoleic acidSMPDB, HMDB, MeSH
(10E,​12Z)-9-HODESMPDB, HMDB, ChEBI
Chemical FormulaC18H32O3
Average Molecular Weight296.451
Monoisotopic Molecular Weight296.23514489
IUPAC Name(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Name(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
CAS Registry Number98524-19-7
SMILES
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])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-ZJHFMPGASA-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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/lALOGPS
LogP5.88ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability37.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.16931661259
DarkChem[M-H]-179.74531661259
DeepCCS[M+H]+194.94430932474
DeepCCS[M-H]-192.58630932474
DeepCCS[M-2H]-226.35930932474
DeepCCS[M+Na]+201.58830932474
AllCCS[M+H]+181.232859911
AllCCS[M+H-H2O]+178.232859911
AllCCS[M+NH4]+183.932859911
AllCCS[M+Na]+184.732859911
AllCCS[M-H]-180.032859911
AllCCS[M+Na-2H]-181.532859911
AllCCS[M+HCOO]-183.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(10E,12Z)-9-HODE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O3635.1Standard polar33892256
(10E,12Z)-9-HODE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O2198.7Standard non polar33892256
(10E,12Z)-9-HODE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O2331.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(10E,12Z)-9-HODE,1TMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)O[Si](C)(C)C2532.9Semi standard non polar33892256
(10E,12Z)-9-HODE,1TMS,isomer #2CCCCC/C=C\C=C\C(O)CCCCCCCC(=O)O[Si](C)(C)C2477.4Semi standard non polar33892256
(10E,12Z)-9-HODE,2TMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2526.7Semi standard non polar33892256
(10E,12Z)-9-HODE,1TBDMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2776.1Semi standard non polar33892256
(10E,12Z)-9-HODE,1TBDMS,isomer #2CCCCC/C=C\C=C\C(O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2722.8Semi standard non polar33892256
(10E,12Z)-9-HODE,2TBDMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3019.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-9-HODE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbc-7950000000-3cfa26df2f485f43ea0b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-9-HODE GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9133100000-615fce6d28e837fb087e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-9-HODE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-9-HODE 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 - (10E,12Z)-9-HODE 10V, Positive-QTOFsplash10-004i-0090000000-cb7f83c104f8b4f7a5d02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 20V, Positive-QTOFsplash10-06ur-5590000000-52b5fc3231b31e1bdbcb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 40V, Positive-QTOFsplash10-0536-9210000000-96c195b6f6a32ccd80792017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 10V, Negative-QTOFsplash10-0002-0090000000-3d5630b842dbad3bc8872017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 20V, Negative-QTOFsplash10-004j-0190000000-9af33ffd09081fae67782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 40V, Negative-QTOFsplash10-0a4l-9720000000-fc7436feeb97b5db2c892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 10V, Positive-QTOFsplash10-004i-1390000000-a7e09426f7a9c09c24cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 20V, Positive-QTOFsplash10-020r-4920000000-81fe8256f00319c682e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 40V, Positive-QTOFsplash10-053r-9300000000-8230ecc50e071c3d6fb42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 10V, Negative-QTOFsplash10-0002-0090000000-7f1bcc096e1ebce2ab9b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 20V, Negative-QTOFsplash10-002b-0190000000-2d737cfe037e964f08f72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-9-HODE 40V, Negative-QTOFsplash10-002f-3920000000-ea7ca0690be4e4de8e222021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link9-Hydroxyoctadecadienoic acid
METLIN IDNot Available
PubChem Compound5282944
PDB IDNot Available
ChEBI ID72651
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.