Record Information
Version1.0
Creation date2011-09-21 00:34:50 UTC
Update date2018-05-29 01:53:08 UTC
Primary IDFDB023796
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20-Hydroxyeicosatetraenoic acid
DescriptionMetabolite produced during NADPH dependent enzymatic oxidation of arachidonic acid. Potent vasoconstrictor [CCD] 20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor or renal, cerebral and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase and the mitogen activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries and that a fall in levels of 20-HETE contributes the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries. (PMID: 16258232) [HMDB]
CAS Number79551-86-3
Structure
Thumb
Synonyms
SynonymSource
20-HydroxyeicosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoateGenerator
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acidChEBI
(all-Z)-20-hydroxy-5,8,11,14-eicosatetraenoatehmdb
(all-Z)-20-hydroxy-5,8,11,14-eicosatetraenoic acidhmdb
20-HETEdb_source
20-Hydroxy arachidonateGenerator
20-Hydroxy arachidonic acidChEBI
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateHMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acidHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoatehmdb
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidhmdb
20-HydroxyarachidonateGenerator
20-Hydroxyarachidonic aciddb_source
20-HydroxyicosatetraenoateGenerator
20-Hydroxyicosatetraenoic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP5.87ALOGPS
logP5.15ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.88 m³·mol⁻¹ChemAxon
Polarizability39.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H32O3
IUPAC name20-hydroxyicosa-5,8,11,14-tetraenoic acid
InChI IdentifierInChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)
InChI KeyNNDIXBJHNLFJJP-UHFFFAOYSA-N
Isomeric SMILESOCCCCCC=CCC=CCC=CCC=CCCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen 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 ID4446281
ChEMBL IDNot Available
KEGG Compound IDC14748
Pubchem Compound ID5283157
Pubchem Substance IDNot Available
ChEBI ID34306
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05998
CRC / DFC (Dictionary of Food Compounds) IDCPV52-M:CPV52-M
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 IDHydroxyeicosatetraenoic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
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