Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:12 UTC
Update Date2021-09-14 15:47:07 UTC
HMDB IDHMDB0010216
Secondary Accession Numbers
  • HMDB10216
Metabolite Identification
Common Name5,15-DiHETE
Description5,15-DiHETE, also known as 5S,15S-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, 5,15-dihete is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 5,15-DiHETE.
Structure
Data?1582752798
Synonyms
ValueSource
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic acidChEBI
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-icosatetraenoic acidChEBI
(5S,6E,8Z,11Z,13E,15S)-5,15-Dihydroxyicosatetraenoic acidChEBI
5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoic acidChEBI
5,15-Dihydroxy-6,8,11,13-eicosatetraenoic acidChEBI
5,15-Dihydroxyeicosatetraenoic acidChEBI
5S,15S-DiHETEChEBI
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acidChEBI
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateGenerator
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-icosatetraenoateGenerator
(5S,6E,8Z,11Z,13E,15S)-5,15-DihydroxyicosatetraenoateGenerator
5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoateGenerator
5,15-Dihydroxy-6,8,11,13-eicosatetraenoateGenerator
5,15-DihydroxyeicosatetraenoateGenerator
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoateGenerator
5(S),15(S)-DiHETEHMDB
5,15-DiHETEChEBI
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid
Traditional Name5S,15S-DiHETE
CAS Registry Number82200-87-1
SMILES
CCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1
InChI KeyUXGXCGPWGSUMNI-BVHTXILBSA-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
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 Solubility0.016 g/LALOGPS
logP5.33ALOGPS
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
Polarizability39.52 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]+189.08431661259
DarkChem[M-H]-188.85231661259
DeepCCS[M+H]+195.85230932474
DeepCCS[M-H]-193.22630932474
DeepCCS[M-2H]-227.78630932474
DeepCCS[M+Na]+203.01330932474
AllCCS[M+H]+190.632859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+193.232859911
AllCCS[M+Na]+194.032859911
AllCCS[M-H]-187.732859911
AllCCS[M+Na-2H]-189.532859911
AllCCS[M+HCOO]-191.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,15-DiHETECCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O4668.3Standard polar33892256
5,15-DiHETECCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O2688.5Standard non polar33892256
5,15-DiHETECCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O2884.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,15-DiHETE,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C2970.9Semi standard non polar33892256
5,15-DiHETE,1TMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C2969.6Semi standard non polar33892256
5,15-DiHETE,1TMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C2896.1Semi standard non polar33892256
5,15-DiHETE,2TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3006.4Semi standard non polar33892256
5,15-DiHETE,2TMS,isomer #2CCCCC[C@@H](/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2953.6Semi standard non polar33892256
5,15-DiHETE,2TMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2953.5Semi standard non polar33892256
5,15-DiHETE,3TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2965.0Semi standard non polar33892256
5,15-DiHETE,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3225.7Semi standard non polar33892256
5,15-DiHETE,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3224.6Semi standard non polar33892256
5,15-DiHETE,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3139.9Semi standard non polar33892256
5,15-DiHETE,2TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\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)C3503.0Semi standard non polar33892256
5,15-DiHETE,2TBDMS,isomer #2CCCCC[C@@H](/C=C/C=C\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)C3442.0Semi standard non polar33892256
5,15-DiHETE,2TBDMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3441.6Semi standard non polar33892256
5,15-DiHETE,3TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\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)C3727.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,15-DiHETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kk-6492000000-3c2ee47ee6c0da2b1c182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,15-DiHETE GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9013440000-ef35dbcf7f2fcff2741e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,15-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 - 5,15-DiHETE 10V, Positive-QTOFsplash10-0gb9-0019000000-f48b85306f04941fd3502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 20V, Positive-QTOFsplash10-106r-4196000000-2bead0468d6c53e9925e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 40V, Positive-QTOFsplash10-0596-9460000000-5fbe33b7844341ee0d012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 10V, Negative-QTOFsplash10-00kr-0029000000-d8e68d87d5e32a76be4d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 20V, Negative-QTOFsplash10-01bi-3069000000-b36c2c202ba716d4d1b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 40V, Negative-QTOFsplash10-0a4l-9040000000-45f4070691efc333f1882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 10V, Positive-QTOFsplash10-0uxr-0019000000-59a1f0edad1bc877238e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 20V, Positive-QTOFsplash10-0udi-2449000000-fb935c85ebd7e2a9b21b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 40V, Positive-QTOFsplash10-014m-9620000000-f3e46e59b0649a6e56bc2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 10V, Negative-QTOFsplash10-00kr-0019000000-c96c619b8b59ea16cad12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 20V, Negative-QTOFsplash10-014r-3289000000-317e4e3f86ab790bd3612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,15-DiHETE 40V, Negative-QTOFsplash10-07be-8291000000-9698a4ac42a43db4361b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000527 +/- 0.000017 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000247 +/- 0.00002 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.00007 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000247 +/- 0.0000200 uMAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027370
KNApSAcK IDNot Available
Chemspider ID4446282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283158
PDB IDNot Available
ChEBI ID91286
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. Borgeat P, Picard S, Drapeau J, Vallerand P: Metabolism of arachidonic acid in leukocytes: isolation of a 5,15-dihydroxy-eicosatetraenoic acid. Lipids. 1982 Oct;17(10):676-81. [PubMed:6817003 ]