Record Information
Version1.0
Creation date2011-09-21 00:29:27 UTC
Update date2015-07-21 06:57:41 UTC
Primary IDFDB023406
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHepoxilin A3
DescriptionHepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937) Hepoxilins have biological actions that appear to have, as their basis, changes in intracellular concentrations of ions including calcium and potassium ions as well as changes in second messenger systems. Recent evidence suggests that the biological actions of the hepoxilins may be receptor-mediated as indicated from data showing the existence of hepoxilin-specific binding proteins in the human neutrophils. Such evidence also implicates the association of G-proteins both in hepoxilin-binding as well as in hepoxilin action. (PMID 7947989) [HMDB]
CAS Number85589-24-8
Structure
Thumb
Synonyms
SynonymSource
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoatehmdb
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acidhmdb
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoatehmdb
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acidhmdb
(5Z,9e,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoateGenerator
(5Z,9e,14Z)-(8XI,11R,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acidChEBI
(5Z,9e,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoateGenerator
(5Z,9e,14Z)-(8XI,11R,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acidChEBI
(5Z,9E)-8-hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoatehmdb
(5Z,9E)-8-hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acidhmdb
8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoatehmdb
8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acidhmdb
8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoatehmdb
8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP5.57ALOGPS
logP4.57ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability40.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O4
IUPAC name8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid
InChI IdentifierInChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/t17?,18-,19+/m0/s1
InChI KeySGTUOBURCVMACZ-JLMCIHFGSA-N
Isomeric SMILES[H][C@@]1(CC=CCCCCC)O[C@]1([H])C=CC(O)CC=CCCCC(O)=O
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
Classification
Description Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHepoxilins
Alternative Parents
Substituents
  • Hepoxilin
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Heterocyclic fatty acid
  • Epoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 ID4573947
ChEMBL IDNot Available
KEGG Compound IDC14808
Pubchem Compound ID5460414
Pubchem Substance IDNot Available
ChEBI ID36190
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04688
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference