16(17)-EpDPE (CHEM041387)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:28 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041387
Identification
Common Name16(17)-EpDPE
ClassSmall Molecule
DescriptionAn EpDPE obtained by formal epoxidation of the 16,17-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
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoic acidChEBI
16,17-EDPChEBI
16,17-Epoxydocosapentaenoic acidChEBI
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoateGenerator
16,17-EpoxydocosapentaenoateGenerator
16(17)-EpDoPEHMDB
Chemical FormulaC22H32O3
Average Molecular Mass344.488 g/mol
Monoisotopic Mass344.235 g/mol
CAS Registry NumberNot Available
IUPAC Name(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid
Traditional Name(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid
SMILESCC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI IdentifierInChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12-
InChI KeyBCTXZWCPBLWCRV-ZYADFMMDSA-N
Chemical Taxonomy
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
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • 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 Solubility0.00027 g/LALOGPS
logP6.16ALOGPS
logP5.81ChemAxon
logS-6.1ALOGPS
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
Polarizability40.41 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, Positivesplash10-00lr-5391000000-eca8613c027ec77114b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0rta-9344100000-eae04a555061ea8367e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1029000000-6aa72f00daadb1ba4c7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017i-9383000000-5a0d6eec821440733720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe3-9630000000-d10dfa768fb9fefdcdc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1029000000-2494b8cd0c2c4c4afa84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-3069000000-9ec5ad4d4f5d363b8019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9020000000-561f45aa1c0eb363a33bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2139000000-6c4dd45859b7c6798121Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-9826000000-b688bc2e69f1c52c2062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9700000000-06fa0665d1492676af5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0039000000-c68ec18fd5d4ac034e16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-2149000000-8efe3784e6b394626646Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9031000000-880d8778f1345dabf38dSpectrum
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 IDHMDB0013621
FooDB IDFDB029598
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21466945
ChEBI ID72855
PubChem Compound ID14392758
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16112640
2. 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.
3. 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.
4. 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.
5. 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.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. The lipid handbook with CD-ROM