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Showing Compound 15(S)-HETE (FDB023242)

Record Information
Version1.0
Creation date2011-09-21 00:26:48 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023242
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15(S)-HETE
Description15(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340) [HMDB]
CAS Number54845-95-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoatehmdb
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acidhmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoatehmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acidhmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acidhmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoatehmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acidhmdb
(15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoateGenerator
(15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoic acidChEBI
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoateGenerator
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoic acidChEBI
(5Z,8Z,11Z,13e,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoateGenerator
(5Z,8Z,11Z,13e,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,13e,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoateGenerator
(5Z,8Z,11Z,13e,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acidChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoatehmdb
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acidhmdb
(S)-15-HETEhmdb
15 HeteHMDB
15-HETEHMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoatehmdb
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acidhmdb
15(S)-HydroxyeicosatetraenoateGenerator
15(S)-Hydroxyeicosatetraenoic acidChEBI
15S-HETEhmdb
15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoatehmdb
15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidhmdb
IcomucretChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP5.82ALOGPS
logP5.36ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name(15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1
InChI KeyJSFATNQSLKRBCI-IBGZPJMESA-N
Isomeric SMILES[H][C@](O)(CCCCC)C=CC=CCC=CCC=CCCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444307
ChEMBL IDCHEMBL594621
KEGG Compound IDC04742
Pubchem Compound ID5280724
Pubchem Substance IDNot Available
ChEBI ID15558
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03876
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutathione peroxidase 7GPX7Q96SL4
Epididymal secretory glutathione peroxidaseGPX5O75715
Glutathione peroxidase 6GPX6P59796
Glutathione peroxidase 1GPX1P07203
Phospholipid hydroperoxide glutathione peroxidase, mitochondrialGPX4P36969
Glutathione peroxidase 3GPX3P22352
Glutathione peroxidase 2GPX2P18283
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference