Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:00:49 UTC
Update Date2022-03-07 03:17:59 UTC
HMDB IDHMDB0062749
Secondary Accession Numbers
  • HMDB62749
Metabolite Identification
Common Name5(S),15(R)-DiHETE
Description5(S),15(R)-DiHETE is also known as 5S,15R-DiHETE or 5S,15R-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoate. 5(S),15(R)-DiHETE is considered to be practically insoluble (in water) and acidic. 5(S),15(R)-DiHETE is an eicosanoid lipid molecule
Structure
Data?1563866355
Synonyms
ValueSource
(5S,6E,8Z,11Z,15R)-5,15-Dihydroxyicosa-6,8,11,13-tetraenoateGenerator
(5S,6E,8Z,11Z,13E,15R)-5,15-DihydroxyicosatetraenoateHMDB
(5S,6E,8Z,11Z,13E,15R)-5,15-Dihydroxyicosatetraenoic acidHMDB
5S,15R-DiHETEHMDB
5S,15R-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoateHMDB
5S,15R-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.472
Monoisotopic Molecular Weight336.23005951
IUPAC Name(5S,6E,8Z,11Z,15R)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid
Traditional Name(5S,6E,8Z,11Z,15R)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O)=C(/[H])C([H])=C([H])[C@]([H])(O)CCCCC
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-/m1/s1
InChI KeyUXGXCGPWGSUMNI-XGASFZMTSA-N
Chemical Taxonomy
ClassificationNot classified
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
LogP5.33ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
Polarizability39.9 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]+188.56431661259
DarkChem[M-H]-189.65531661259
DeepCCS[M+H]+189.61930932474
DeepCCS[M-H]-187.79430932474
DeepCCS[M-2H]-221.26930932474
DeepCCS[M+Na]+195.22530932474
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(S),15(R)-DiHETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O)=C(/[H])C([H])=C([H])[C@]([H])(O)CCCCC4370.2Standard polar33892256
5(S),15(R)-DiHETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O)=C(/[H])C([H])=C([H])[C@]([H])(O)CCCCC2551.4Standard non polar33892256
5(S),15(R)-DiHETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])[C@@]([H])(O)CCCC(O)=O)=C(/[H])C([H])=C([H])[C@]([H])(O)CCCCC2723.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5(S),15(R)-DiHETE,1TMS,isomer #1CCCCC[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(S),15(R)-DiHETE,1TMS,isomer #2CCCCC[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(S),15(R)-DiHETE,1TMS,isomer #3CCCCC[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(S),15(R)-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(S),15(R)-DiHETE,2TMS,isomer #2CCCCC[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(S),15(R)-DiHETE,2TMS,isomer #3CCCCC[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(S),15(R)-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(S),15(R)-DiHETE,1TBDMS,isomer #1CCCCC[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(S),15(R)-DiHETE,1TBDMS,isomer #2CCCCC[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(S),15(R)-DiHETE,1TBDMS,isomer #3CCCCC[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(S),15(R)-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(S),15(R)-DiHETE,2TBDMS,isomer #2CCCCC[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(S),15(R)-DiHETE,2TBDMS,isomer #3CCCCC[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(S),15(R)-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(S),15(R)-DiHETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mk-6593000000-2751a1ab8fa609ec22232017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),15(R)-DiHETE GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9013440000-ef35dbcf7f2fcff2741e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),15(R)-DiHETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S),15(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),15(R)-DiHETE 10V, Positive-QTOFsplash10-0gb9-0019000000-f48b85306f04941fd3502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 20V, Positive-QTOFsplash10-106r-4196000000-457cb39a0c8a1268151f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 40V, Positive-QTOFsplash10-0596-9460000000-1d8ccbfff9f2085449352017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 10V, Negative-QTOFsplash10-00kr-0029000000-d8e68d87d5e32a76be4d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 20V, Negative-QTOFsplash10-01bi-3069000000-b36c2c202ba716d4d1b92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 40V, Negative-QTOFsplash10-0a4l-9040000000-37f888cda0004f79ffde2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 10V, Negative-QTOFsplash10-014s-0049000000-784325c131ef5c44fce12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 20V, Negative-QTOFsplash10-0aor-9188000000-15277ba1c4c98244623c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 40V, Negative-QTOFsplash10-0592-6190000000-ca8869c75c9dfdfc3d952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 10V, Positive-QTOFsplash10-0gb9-0169000000-f816e4fd4e2a085194c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 20V, Positive-QTOFsplash10-0udj-1094000000-99ee8f680bdef2d949ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S),15(R)-DiHETE 40V, Positive-QTOFsplash10-05mk-3890000000-910cf30a3a4ead5de99e2021-09-22Wishart 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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.