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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:41:51 UTC
Update Date2022-03-07 03:17:52 UTC
HMDB IDHMDB0062290
Secondary Accession Numbers
  • HMDB62290
Metabolite Identification
Common Name12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid
Description12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid, also known as 12(R)DH-HETE, is classified as a member of the Hydroxyeicosatrienoic acids. Hydroxyeicosatrienoic acids are eicosanoic acids with an attached hydroxyl group and three CC double bonds. 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid is considered to be practically insoluble (in water) and acidic. 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid is an eicosanoid lipid molecule
Structure
Data?1563866291
Synonyms
ValueSource
12-Hydroxy-5,8,14-eicosatrienoic acidMeSH
12-Hydroxy-5,8,14-eicosatrienoic acid, (S-(Z,Z,Z))-isomerMeSH
12-Hydroxy-5,8,14-eicosatrienoic acid, (Z,Z,Z)-isomerMeSH
12R-Hydroxy-5Z,8Z,12Z-eicosatrienoateGenerator
12(R)DH-HETEHMDB
Chemical FormulaC20H34O3
Average Molecular Weight322.489
Monoisotopic Molecular Weight322.250794955
IUPAC Name(5Z,8Z,12R,14Z)-12-hydroxyicosa-5,8,14-trienoic acid
Traditional Name12R-HETrE
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC
InChI Identifier
InChI=1S/C20H34O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13,19,21H,2-6,12,14-18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-/t19-/m0/s1
InChI KeyRFAKHEWADWLSJX-ZIQRGBBDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • 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 Solubility0.0011 g/lALOGPS
LogP6.11ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.11ALOGPS
logP5.56ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.51 m³·mol⁻¹ChemAxon
Polarizability39.41 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]+188.28531661259
DarkChem[M-H]-188.82431661259
DeepCCS[M+H]+192.32330932474
DeepCCS[M-H]-190.2630932474
DeepCCS[M-2H]-223.49930932474
DeepCCS[M+Na]+198.23630932474
AllCCS[M+H]+188.532859911
AllCCS[M+H-H2O]+185.732859911
AllCCS[M+NH4]+191.132859911
AllCCS[M+Na]+191.932859911
AllCCS[M-H]-187.132859911
AllCCS[M+Na-2H]-189.032859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC4056.3Standard polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC2446.9Standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC2625.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TMS,isomer #1CCCCC/C=C\C[C@H](O)CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2551.9Semi standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TMS,isomer #2CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2629.3Semi standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,2TMS,isomer #1CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2589.1Semi standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TBDMS,isomer #1CCCCC/C=C\C[C@H](O)CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2802.6Semi standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2885.0Semi standard non polar33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,2TBDMS,isomer #1CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3094.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r7-8972000000-fe07cc3c317f890829a82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0209-9243200000-b09e11f574f4ad0f65092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic 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 - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Positive-QTOFsplash10-0a4i-0049000000-61e9a2d385df4e0087162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Positive-QTOFsplash10-0a4i-5894000000-aa2e090c39cd912a725a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Positive-QTOFsplash10-059f-9730000000-64abc201b67c6a9400782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Negative-QTOFsplash10-00di-0019000000-872177841a61153a72142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Negative-QTOFsplash10-0uk9-1249000000-cbee8665c1ba104ab63b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Negative-QTOFsplash10-0a4l-9820000000-4714bd7856935e2c10072017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Positive-QTOFsplash10-0ab9-2329000000-4435dd80c7748c1716cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Positive-QTOFsplash10-052u-6942000000-a013aabce47a0bcf337c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Positive-QTOFsplash10-00l6-9300000000-dda8a60055a787f4a7b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Negative-QTOFsplash10-00di-0009000000-ddad7bbed5e6056bf9d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Negative-QTOFsplash10-0uk9-0239000000-16f5e2aed445bc7c60282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Negative-QTOFsplash10-052f-9541000000-4c9b81cc674737f6ba752021-09-24Wishart 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 LinkNot Available
METLIN IDNot Available
PubChem Compound5283149
PDB IDNot Available
ChEBI IDNot Available
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.