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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:15:32 UTC
Update Date2021-09-14 14:57:52 UTC
HMDB IDHMDB0062409
Secondary Accession Numbers
  • HMDB62409
Metabolite Identification
Common Name5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid
Description5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid is classified as a member of the Leukotrienes. Leukotrienes are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid is an eicosanoid lipid molecule
Structure
Data?1563866308
Synonyms
ValueSource
5,12-Dihydroxy-6,8,10,14-eicosatetraenoateGenerator
Chemical FormulaC20H32O4
Average Molecular Weight336.472
Monoisotopic Molecular Weight336.23005951
IUPAC Name(6E,8E,10E,14E)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name5,12-DiHETE
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=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/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6+,14-10+,15-11+
InChI KeyVNYSSYRCGWBHLG-XUOUMLBJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/lALOGPS
LogP5.46ALOGPS
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(5.46) g/LALOGPS
logP10(4.13) 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 Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability41.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.22731661259
DarkChem[M-H]-190.13731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TMS,#1CCCCC/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C2982.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TMS,#2CCCCC/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C2982.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TMS,#3CCCCC/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C2884.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TMS,#1CCCCC/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3010.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TMS,#2CCCCC/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2914.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TMS,#3CCCCC/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2922.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,3TMS,#1CCCCC/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)C2926.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TBDMS,#1CCCCC/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3230.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TBDMS,#2CCCCC/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C3225.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,1TBDMS,#3CCCCC/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C3115.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TBDMS,#1CCCCC/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)C3464.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TBDMS,#2CCCCC/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)C3394.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,2TBDMS,#3CCCCC/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)C3406.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid,3TBDMS,#1CCCCC/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)C3658.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
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 Compound5312972
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.