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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:41:34 UTC
Update Date2022-03-07 03:17:57 UTC
HMDB IDHMDB0062615
Secondary Accession Numbers
  • HMDB62615
Metabolite Identification
Common Name5(S),11(R)-DiHETE
Description5(S),11(R)-DiHETE, also known as 5,11-dihete, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 5(S),11(R)-dihete is considered to be an eicosanoid lipid molecule. 5(S),11(R)-DiHETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866337
Synonyms
ValueSource
(5S,6E,8Z,11R,12E,14Z)-5,11-Dihydroxyicosatetraenoic acidChEBI
5,11-DiHETEChEBI
5S,11R-DiHETEChEBI
5S,11R-Dihydroxy-6E,8Z,12E,14Z-eicosatetraenoic acidChEBI
(5S,6E,8Z,11R,12E,14Z)-5,11-DihydroxyicosatetraenoateGenerator
5S,11R-Dihydroxy-6E,8Z,12E,14Z-eicosatetraenoateGenerator
Chemical FormulaC20H32O4
Average Molecular Weight336.472
Monoisotopic Molecular Weight336.23005951
IUPAC Name(5S,6E,8Z,11R,12E,14Z)-5,11-dihydroxyicosa-6,8,12,14-tetraenoic acid
Traditional Name5,11-diHETE
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(O)C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-9-13-18(21)14-10-8-11-15-19(22)16-12-17-20(23)24/h6-11,13,15,18-19,21-22H,2-5,12,14,16-17H2,1H3,(H,23,24)/b7-6-,10-8-,13-9+,15-11+/t18-,19+/m0/s1
InChI KeyGVBURXXHWSCJSI-ZZHGHEOFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic 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 Solubility0.016 g/lALOGPS
LogP5.39ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.39ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability40.36 ųChemAxon
Number of Rings0ChemAxon
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]+189.92431661259
DarkChem[M-H]-187.531661259
DeepCCS[M+H]+199.94930932474
DeepCCS[M-H]-198.12430932474
DeepCCS[M-2H]-231.36530932474
DeepCCS[M+Na]+205.55530932474
AllCCS[M+H]+190.832859911
AllCCS[M+H-H2O]+188.032859911
AllCCS[M+NH4]+193.432859911
AllCCS[M+Na]+194.132859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-189.732859911
AllCCS[M+HCOO]-191.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5(S),11(R)-DiHETE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(O)C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O4366.3Standard polar33892256
5(S),11(R)-DiHETE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(O)C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O2544.5Standard non polar33892256
5(S),11(R)-DiHETE[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(O)C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O2700.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5(S),11(R)-DiHETE,1TMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@@H](O)CCCC(=O)O)O[Si](C)(C)C2961.9Semi standard non polar33892256
5(S),11(R)-DiHETE,1TMS,isomer #2CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@H](CCCC(=O)O)O[Si](C)(C)C2946.2Semi standard non polar33892256
5(S),11(R)-DiHETE,1TMS,isomer #3CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@@H](O)CCCC(=O)O[Si](C)(C)C2870.3Semi standard non polar33892256
5(S),11(R)-DiHETE,2TMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2994.7Semi standard non polar33892256
5(S),11(R)-DiHETE,2TMS,isomer #2CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2934.7Semi standard non polar33892256
5(S),11(R)-DiHETE,2TMS,isomer #3CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2925.7Semi standard non polar33892256
5(S),11(R)-DiHETE,3TMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2953.8Semi standard non polar33892256
5(S),11(R)-DiHETE,1TBDMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3218.0Semi standard non polar33892256
5(S),11(R)-DiHETE,1TBDMS,isomer #2CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3196.7Semi standard non polar33892256
5(S),11(R)-DiHETE,1TBDMS,isomer #3CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3120.1Semi standard non polar33892256
5(S),11(R)-DiHETE,2TBDMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3479.5Semi standard non polar33892256
5(S),11(R)-DiHETE,2TBDMS,isomer #2CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3416.1Semi standard non polar33892256
5(S),11(R)-DiHETE,2TBDMS,isomer #3CCCCC/C=C\C=C\[C@H](O)C/C=C\C=C[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3410.8Semi standard non polar33892256
5(S),11(R)-DiHETE,3TBDMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C=C[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3704.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),11(R)-DiHETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-7796000000-f59af64733a07c968fa32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),11(R)-DiHETE GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9013540000-66d84a120df1b671d2452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),11(R)-DiHETE 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 - 5(S),11(R)-DiHETE 10V, Positive-QTOFsplash10-0gb9-0019000000-96894e347f4484cc92592017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 20V, Positive-QTOFsplash10-106r-4789000000-cd79db6788cf3f1b3dc22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 40V, Positive-QTOFsplash10-059f-9450000000-bd7f580682376ced9e4d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 10V, Negative-QTOFsplash10-00kr-0029000000-bcf535ff1b1e95bf7a8d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 20V, Negative-QTOFsplash10-01bi-2269000000-4000d6578be1bda5ff012017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 40V, Negative-QTOFsplash10-0a4l-9340000000-05fd29ef63d0c76532732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 10V, Negative-QTOFsplash10-000i-0109000000-34dcc056ad790fbb8af42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 20V, Negative-QTOFsplash10-014r-2389000000-431f5f19b23d4447f0032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 40V, Negative-QTOFsplash10-004i-3490000000-45d3972751fb69d893f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 10V, Positive-QTOFsplash10-0gb9-0319000000-27ab4c9f1f2f57a35d772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 20V, Positive-QTOFsplash10-0v00-4669000000-f8b78f6fde1b8f10b63a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),11(R)-DiHETE 40V, Positive-QTOFsplash10-014i-9510000000-421b3c403987bd2b47de2021-09-25Wishart 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 Compound45104915
PDB IDNot Available
ChEBI ID91136
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.