12(13)Ep-9-KODE (CHEM041388)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:30 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041388
Identification
Common Name12(13)Ep-9-KODE
ClassSmall Molecule
Descriptiontrans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid is formed from 13-L (S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid by a cysteine • FeCl3 redox couple in the presence of O2 (PMID: 7284410).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
trans-12,13-Epoxy-11-oxo-trans-9-octadecenoateHMDB
trans-12,13-Epoxy-11-oxo-trans-9-octadecenoic acidHMDB
9-oxo-12,13-Epoxy-10-octadecenoateGenerator
12,13-Epoxy-11-oxo-9-octadecenoic acidMeSH
EPOODAMeSH
Chemical FormulaC18H30O4
Average Molecular Mass310.428 g/mol
Monoisotopic Mass310.214 g/mol
CAS Registry NumberNot Available
IUPAC Name(10E)-9-oxo-11-(3-pentyloxiran-2-yl)undec-10-enoic acid
Traditional Name(10E)-9-oxo-11-(3-pentyloxiran-2-yl)undec-10-enoic acid
SMILESCCCCCC1OC1\C=C\C(=O)CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H30O4/c1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h13-14,16-17H,2-12H2,1H3,(H,20,21)/b14-13+
InChI KeyRCMABBHQYMBYKV-BUHFOSPRSA-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
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen 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 Solubility0.0046 g/LALOGPS
logP4.37ALOGPS
logP4.82ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity87.39 m³·mol⁻¹ChemAxon
Polarizability37.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap3-9170000000-5f3eac6a7bbc3e9333b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-053f-9032000000-f0bea7dcd3ff1c9d260fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1292000000-bd30d421875fdd14dde1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00o9-9530000000-97c002303c5faef11c3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05no-9310000000-c2bac41b9a445d6da919Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0259000000-7406d95c06f54c8f5afbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0apl-2942000000-d40a5bbdaa23b1eaf455Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9510000000-2209075a31d2d6df1933Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0292000000-7e6ff5bb1b4e75f15b5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tc-3491000000-329fc8e734bf1358d1b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9200000000-f257d8e40103132940c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-f247e6f056aac64f82c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-2896000000-674c1c62285ce8095bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-8970000000-25f25f888b8a95384a66Spectrum
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 IDHMDB0013623
FooDB IDFDB029600
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446134
ChEBI ID89606
PubChem Compound ID5283007
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gardner HW, Crawford CG: Degradation of linoleic acid hydroperoxides by a cysteine . FeCl3 catalyst as a model for similar biochemical reactions. III. A novel product, trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid, from 13-L (S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid. Biochim Biophys Acta. 1981 Jul 24;665(1):126-33.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM