Record Information
Version1.0
Creation date2011-09-21 00:22:24 UTC
Update date2015-07-21 06:57:26 UTC
Primary IDFDB022960
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8,9-DiHETrE
Description8,9-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid (AA) metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. P450converts AA to 8,9- dihydroxyeicosatrienoic acid. This enzymatic pathway was first described in liver; however, it is now clear that AA can be metabolized by P450 in many tissues including the pituitary gland, eye, kidney, adrenal gland, and blood vessels. (PMID: 17431031, 11700990) [HMDB]
CAS Number192461-96-4
Structure
Thumb
Synonyms
SynonymSource
(+/-)8,9-Dihetrehmdb
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoatehmdb
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoic acidhmdb
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoatehmdb
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoic acidhmdb
8,9-DHEThmdb
8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoatehmdb
8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoic acidhmdb
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoateGenerator
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoic acidChEBI
8,9-dihydroxyeicosatrienoatehmdb
8,9-dihydroxyeicosatrienoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP5.44ALOGPS
logP4.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.87 m³·mol⁻¹ChemAxon
Polarizability39.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O4
IUPAC name8,9-dihydroxyicosa-5,11,14-trienoic acid
InChI IdentifierInChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)
InChI KeyDCJBINATHQHPKO-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC(O)C(O)CC=CCCCC(O)=O
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
Classification
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
  • 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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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 ID4446268
ChEMBL IDNot Available
KEGG Compound IDC14773
Pubchem Compound ID5283144
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02311
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
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference