Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006940
Secondary Accession Numbers
  • HMDB06940
Metabolite Identification
Common Name9(S)-HPODE
Description9(S)-HPODE 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. 9(S)-HPODE is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752415
Synonyms
ValueSource
(10E,12Z)-9-Hydroperoxyoctadeca-10,12-dienoateHMDB
Chemical FormulaC18H32O4
Average Molecular Weight312.4443
Monoisotopic Molecular Weight312.230059512
IUPAC Name(10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
Traditional Name9(S)-hpode
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C=C/C(CCCCCCCC(O)=O)OO
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+
InChI KeyJGUNZIWGNMQSBM-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
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.0037 g/LALOGPS
logP5.74ALOGPS
logP5.64ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.38 m³·mol⁻¹ChemAxon
Polarizability37.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.83431661259
DarkChem[M-H]-183.29831661259
DeepCCS[M+H]+184.54530932474
DeepCCS[M-H]-181.99430932474
DeepCCS[M-2H]-215.7230932474
DeepCCS[M+Na]+192.00930932474
AllCCS[M+H]+184.732859911
AllCCS[M+H-H2O]+181.832859911
AllCCS[M+NH4]+187.432859911
AllCCS[M+Na]+188.132859911
AllCCS[M-H]-182.732859911
AllCCS[M+Na-2H]-184.332859911
AllCCS[M+HCOO]-186.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9(S)-HPODECCCCC\C=C/C=C/C(CCCCCCCC(O)=O)OO3857.2Standard polar33892256
9(S)-HPODECCCCC\C=C/C=C/C(CCCCCCCC(O)=O)OO2322.2Standard non polar33892256
9(S)-HPODECCCCC\C=C/C=C/C(CCCCCCCC(O)=O)OO2460.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9(S)-HPODE,1TMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O[Si](C)(C)C)OO2599.7Semi standard non polar33892256
9(S)-HPODE,1TBDMS,isomer #1CCCCC/C=C\C=C\C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO2845.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9(S)-HPODE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9440000000-c657de287e00351c2dd52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9(S)-HPODE GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9533000000-12686f18ef669f1398672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9(S)-HPODE 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 - 9(S)-HPODE 10V, Positive-QTOFsplash10-0002-0192000000-4f03d2f2bc968d55402e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 20V, Positive-QTOFsplash10-066s-5590000000-305c0b420ee5d598e5b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 40V, Positive-QTOFsplash10-0536-9320000000-09fa315035194ffdf2c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 10V, Negative-QTOFsplash10-03di-0149000000-4a41775c40edba3c555e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 20V, Negative-QTOFsplash10-01ox-1693000000-822907c2888d3b6c86e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 40V, Negative-QTOFsplash10-0abc-9730000000-1e8118a529f287df673d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 10V, Negative-QTOFsplash10-03di-0049000000-47c36f2ca86e048d6e572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 20V, Negative-QTOFsplash10-03fr-0294000000-0f62e8df9cde9f695f862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 40V, Negative-QTOFsplash10-0573-6950000000-fa0435ffe57a382744c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 10V, Positive-QTOFsplash10-03fr-1392000000-c52ebf9ba7e2a5cdb0eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 20V, Positive-QTOFsplash10-07lj-9740000000-ca96197990baa307655f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(S)-HPODE 40V, Positive-QTOFsplash10-05q9-9300000000-ebc1e1072f5c33a44ea02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00514 +/- 0.0038 uMAdult (>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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4944227
KEGG Compound IDC14827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439847
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDM01217
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid to 15S-hydroperoxyeicosatetraenoic acid. Also acts on C-12 of arachidonate as well as on linoleic acid.
Gene Name:
ALOX15
Uniprot ID:
P16050
Molecular weight:
74803.795