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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:15:30 UTC
Update Date2022-03-07 03:17:54 UTC
HMDB IDHMDB0062408
Secondary Accession Numbers
  • HMDB62408
Metabolite Identification
Common Name5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
Description5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is classified as a member of the Hydroxyeicosapentaenoic acids. Hydroxyeicosapentaenoic acids are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is considered to be practically insoluble (in water) and acidic. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is an eicosanoid lipid molecule
Structure
Data?1563866307
Synonyms
ValueSource
5S-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoateGenerator
Chemical FormulaC20H30O3
Average Molecular Weight318.457
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5S,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
Traditional Name5S-hepe
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChI KeyFTAGQROYQYQRHF-GHWNLOBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosapentaenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosapentaenoic 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 Solubility0.0029 g/lALOGPS
LogP5.54ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.54ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability38.04 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]+186.55331661259
DarkChem[M-H]-184.34931661259
DeepCCS[M+H]+199.39430932474
DeepCCS[M-H]-197.56930932474
DeepCCS[M-2H]-230.80930932474
DeepCCS[M+Na]+205.030932474
AllCCS[M+H]+185.632859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.432859911
AllCCS[M+Na]+189.232859911
AllCCS[M-H]-183.632859911
AllCCS[M+Na-2H]-185.332859911
AllCCS[M+HCOO]-187.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O4276.1Standard polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O2366.5Standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O2609.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C2767.9Semi standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C2639.4Semi standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2718.3Semi standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3014.0Semi standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C2889.0Semi standard non polar33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TBDMS,isomer #1CC/C=C\C/C=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)C3194.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5394000000-3c896430e353b0ced0db2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0umj-8209200000-58c4694ad173b557f3c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic 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 - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOFsplash10-0udi-0149000000-dfe33b6babf270b347522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOFsplash10-0udu-5693000000-fb5c896d30ace0c553d82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOFsplash10-000l-9880000000-5d7665b416fe42c2c3712017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOFsplash10-014i-0069000000-023fef6c61163c7bc8172017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOFsplash10-00kb-2093000000-e62551450dc40c949d522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOFsplash10-0a4l-9160000000-b435064b3bb6876f2d7b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOFsplash10-0udi-1559000000-04ab13d626af1b8264442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOFsplash10-0kha-4941000000-506babd9193b9c28a9762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOFsplash10-00nf-9500000000-1b5d43f5a2984de189472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOFsplash10-014i-0019000000-c5853cf372543090df7d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOFsplash10-066r-5297000000-8a9ce241f524b80527f12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOFsplash10-0a4m-9840000000-d55d013e9ad27e3eb6512021-09-24Wishart 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 Compound5283193
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.