Showing metabocard for Levuglandin E2 (BMDB0002363)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:54:36 UTC
Update Date2020-04-22 15:10:48 UTC
BMDB IDBMDB0002363
Secondary Accession Numbers
  • BMDB02363
Metabolite Identification
Common NameLevuglandin E2
DescriptionLevuglandin E2, also known as LGE2, 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. Thus, levuglandin E2 is considered to be an eicosanoid. Based on a literature review very few articles have been published on Levuglandin E2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoateHMDB
10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acidHMDB
LGE2HMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
Traditional Name(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
CAS Registry Number91712-41-3
SMILES
CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O
InChI Identifier
InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+/m0/s1
InChI KeyWJWAORNTZNRHBP-LBONXFAWSA-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
  • Branched fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.52ALOGPS
logP3.36ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.54 m³·mol⁻¹ChemAxon
Polarizability40.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9263000000-296c4cb7515a1b701ad6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009x-9211700000-b71612e5c817a13ff0ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-126b7b23bc39fcdf3250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4589000000-1ae21424ce78470e10f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9351000000-c53c0dbb0d045d1c9b2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9ccba837b9402891d62bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fsi-1927000000-5696407cfccd87b39eeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9510000000-72d76c85a734ac002076View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-0129000000-7e6a9daa4876d6b8223fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avj-9365000000-1c01e58986a6aa66a04eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-9410000000-e23687ff0d093af89b31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0019000000-b418a2943f101d719110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uec-3459000000-fcf04b5aafdc13ca87cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9641000000-6c6e011bd1ef9ed2b717View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002363
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022979
KNApSAcK IDNot Available
Chemspider ID30776554
KEGG Compound IDC13807
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevuglandin
METLIN IDNot Available
PubChem Compound5282261
PDB IDNot Available
ChEBI ID34821
References
Synthesis ReferenceMiller, Donald B.; Raychaudhuri, Swadesh R.; Avasthi, Kamlakar; Lal, Kasturi; Levison, Bruce; Salomon, Robert G. Prostaglandin endoperoxides. 25 Levuglandin E2: enantiocontrolled total synthesis of a biologically active rearrangement product from the prostaglandin endoperoxide PGH2. J. Org. Chem. 1990(55) 3164-3175
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available