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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:41:53 UTC
Update Date2019-07-23 07:18:11 UTC
HMDB IDHMDB0062291
Secondary Accession Numbers
  • HMDB62291
Metabolite Identification
Common Name15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid
Description15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid, also known as 13,14-dihydro-15-keto-lipoxin A4 or DHK-lxa4, belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. 15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866291
Synonyms
ValueSource
13,14-Dihydro-15-keto-lipoxin a4ChEBI
13,14-Dihydro-15-keto-lxa4ChEBI
DHK-LXA4ChEBI
15-oxo-5S,6R-Dihydroxy-7E,9E,11Z-eicosatrienoateGenerator
Chemical FormulaC20H32O5
Average Molecular Weight352.471
Monoisotopic Molecular Weight352.22497413
IUPAC Name(5S,6R,7E,9E,11Z)-5,6-dihydroxy-15-oxoicosa-7,9,11-trienoic acid
Traditional Namedhk-LXA4
CAS Registry NumberNot Available
SMILES
[H]\C(CCC(=O)CCCCC)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])[C@@]([H])(O)[C@@]([H])(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,10,14,18-19,22-23H,2-3,8-9,11-13,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,14-10+/t18-,19+/m1/s1
InChI KeyFPRPRBFSKMFXRV-JWVNNVTNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Secondary alcohol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.042 g/lALOGPS
LogP3.57ALOGPS
Predicted Properties
PropertyValueSource
logP3.57ALOGPS
logP3.46ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.36 m³·mol⁻¹ChemAxon
Polarizability41.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ti-7962000000-ed25fb58578576d97f69Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0zi0-9013740000-cee3ef99b520803d2b19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-ca521c3d06c562e77a7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9254000000-a28a5d8914f2d6b5c722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9220000000-767c06f5b5a52f0a711fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-16eb68133f871d8454a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-5589000000-50f30aad83d3e4c2b081Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9640000000-828d47bcc7f668eea5d9Spectrum
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 Compound52921885
PDB IDNot Available
ChEBI ID63993
Food Biomarker OntologyNot Available
VMH 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.