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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 02:10:37 UTC
Update Date2021-09-14 14:58:46 UTC
HMDB IDHMDB0062486
Secondary Accession Numbers
  • HMDB62486
Metabolite Identification
Common Name5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid
Description(6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid 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 (6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866318
Synonyms
ValueSource
(6E,8E,10E,14E,17E)-5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoateGenerator
5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoateGenerator
Leukotriene b5HMDB
LTB 5HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.456
Monoisotopic Molecular Weight334.214409446
IUPAC Name(6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid
Traditional Name5,12-DiHEPE
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6+,14-10+,15-11+
InChI KeyBISQPGCQOHLHQK-RUEGXZCXSA-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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.016 g/lALOGPS
LogP4.68ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(4.68) g/LALOGPS
logP10(3.76) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity104.1 m³·mol⁻¹ChemAxon
Polarizability40.52 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]+192.3731661259
DarkChem[M-H]-189.59331661259
DeepCCS[M+H]+210.26330932474
DeepCCS[M-H]-208.43830932474
DeepCCS[M-2H]-241.67930932474
DeepCCS[M+Na]+215.86930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O4609.8Standard polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O2386.3Standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O2735.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C2990.2Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #2CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C2996.0Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #3CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C2878.9Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3022.2Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #2CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2925.7Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #3CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2932.0Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2919.5Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3236.8Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #2CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C3235.7Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #3CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C3112.2Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3467.2Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #2CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3392.4Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #3CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3401.3Semi standard non polar33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TBDMS,isomer #1CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(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)C3660.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-5976000000-1308051082500b532d7b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9114550000-fb98f8ad419bf0e2f1eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-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 - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOFsplash10-014j-0089000000-945a81862277ca8ffccd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOFsplash10-00kk-3492000000-1307f5bf34685a04ff672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOFsplash10-0a4u-9550000000-dd3a21bd0ec9a9c3281b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOFsplash10-00lr-0029000000-aea24fc310a30c0083f42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOFsplash10-0159-2359000000-2767c62677c595b5c6212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOFsplash10-0a4l-9440000000-c5ad6a89519cdea928ca2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOFsplash10-0159-0019000000-ebe312919323a70b435d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOFsplash10-00lr-3449000000-33dea2da13cb74cad0bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOFsplash10-059l-5391000000-da0f2fad428f71a9a01d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOFsplash10-00kb-0196000000-fb8a4628f13adee8bffa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOFsplash10-0002-1391000000-01dd8cbef267af45ff7a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOFsplash10-0ar0-9610000000-b9ceb4ac3bd3c9071f0a2021-09-25Wishart 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 Compound5312988
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.