19(20)-EpDPE (CHEM041386)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:27 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041386
Identification
Common Name19(20)-EpDPE
ClassSmall Molecule
DescriptionAn EpDPE obtained by formal epoxidation of the 19,20-double bond of docosa-4,7,10,13,16,19-hexaenoic acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidChEBI
19,20-EDPChEBI
19,20-Epoxydocosapentaenoic acidChEBI
19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoateGenerator
19,20-EpoxydocosapentaenoateGenerator
19(20)-EpDoPEHMDB
Epox 22:6n3HMDB
Chemical FormulaC22H32O3
Average Molecular Mass344.488 g/mol
Monoisotopic Mass344.235 g/mol
CAS Registry NumberNot Available
IUPAC Name(4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid
Traditional Name(4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid
SMILESCCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI IdentifierInChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14-
InChI KeyOSXOPUBJJDUAOJ-MBYQGORISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.17ALOGPS
logP5.81ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity109.79 m³·mol⁻¹ChemAxon
Polarizability40.02 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-5491000000-06e9feded58033b38afbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g1-9244000000-98eaf576b716425a6e1dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1029000000-bf092b5708f301ca5c48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-4192000000-e7bc6fe81c4cf10494beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9580000000-4d0b3bd18f872ae4698bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-66522a6a74b8576270e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-4059000000-a2411e92e43b689c02b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9020000000-7466d099ee6fc10bdd74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-6acea8536415463629f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2039000000-6fd5d5db853015562c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9055000000-b5d027e9f2ef45a96e5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-2149000000-11f855435a160fefd89dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ara-4596000000-76c25ecbd1516e1574e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-6900000000-0a062778197c8cbc0d1cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013620
FooDB IDFDB029597
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9806310
ChEBI ID72653
PubChem Compound ID11631565
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Serhan CN, Hong S, Gronert K, Colgan SP, Devchand PR, Mirick G, Moussignac RL: Resolvins: a family of bioactive products of omega-3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals. J Exp Med. 2002 Oct 21;196(8):1025-37.
2. Chataigneau T, Feletou M, Duhault J, Vanhoutte PM: Epoxyeicosatrienoic acids, potassium channel blockers and endothelium-dependent hyperpolarization in the guinea-pig carotid artery. Br J Pharmacol. 1998 Feb;123(3):574-80.
3. Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, Busse R: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature. 1999 Sep 30;401(6752):493-7.
4. Baron A, Frieden M, Beny JL: Epoxyeicosatrienoic acids activate a high-conductance, Ca(2+)-dependent K + channel on pig coronary artery endothelial cells. J Physiol. 1997 Nov 1;504 ( Pt 3):537-43.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. 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.
7. 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.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. The lipid handbook with CD-ROM