Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:42:27 UTC
Update Date2022-03-07 03:17:57 UTC
HMDB IDHMDB0062619
Secondary Accession Numbers
  • HMDB62619
Metabolite Identification
Common Name(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid
Description(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid, also known as Hepoxilin a3 or 8-EH-2, is classified as a member of the Hepoxilins. Hepoxilins are eicosanoids containing an oxirane group attached to the fatty acyl chain. (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid is considered to be practically insoluble (in water) and acidic
Structure
Data?1563866337
Synonyms
ValueSource
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoateKegg
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic acidGenerator
Hepoxilin aMeSH
8-EH-2MeSH
Hexophilin a3MeSH
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acidMeSH
HXA3 CPDMeSH
Hepoxilin a3KEGG
Chemical FormulaC20H32O4
Average Molecular Weight336.472
Monoisotopic Molecular Weight336.23005951
IUPAC Name(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid
Traditional Name(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18?,19-/m0/s1
InChI KeySGTUOBURCVMACZ-NSIHWEAISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHepoxilins
Alternative Parents
Substituents
  • Hepoxilin
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility0.0094 g/lALOGPS
LogP5.57ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.57ALOGPS
logP4.57ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability39.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.89731661259
DarkChem[M-H]-185.38631661259
DeepCCS[M+H]+195.08130932474
DeepCCS[M-H]-193.25630932474
DeepCCS[M-2H]-226.49930932474
DeepCCS[M+Na]+200.68730932474
AllCCS[M+H]+192.032859911
AllCCS[M+H-H2O]+189.232859911
AllCCS[M+NH4]+194.632859911
AllCCS[M+Na]+195.332859911
AllCCS[M-H]-190.132859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-193.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC4187.0Standard polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC2485.7Standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC2620.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #1CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C2637.7Semi standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #2CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C2738.1Semi standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TMS,isomer #1CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2689.9Semi standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #1CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2898.3Semi standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #2CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2981.7Semi standard non polar33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TBDMS,isomer #1CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3168.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0403-4973000000-68b05a5879abdd2702ca2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-9504200000-b478b5ac38b9ea2481202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 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 - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOFsplash10-014i-0119000000-f183a896d40b122d34a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOFsplash10-0100-3923000000-55a8fa7b860b766307572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOFsplash10-05tf-9320000000-806f2e69b92eec98be142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOFsplash10-000i-0029000000-babbe7e5cbfec6729e522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOFsplash10-014r-1849000000-46fca9cc7712fb3e78762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOFsplash10-0a4l-9510000000-19c94ffaa2521c24fe092017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOFsplash10-000i-0009000000-4284d12526c8969005972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOFsplash10-000i-0697000000-b6393912f77c76528f022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOFsplash10-0035-2961000000-b6e6a2b7949fd45ad2062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOFsplash10-014r-2229000000-797f9fb3ace53b814b602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOFsplash10-0kxr-7986000000-202c1560017bfda5161a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOFsplash10-00pi-9300000000-94a32c143312056553eb2021-09-22Wishart 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 IDC04849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHepoxilin
METLIN IDNot Available
PubChem Compound5280743
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDC04849
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.