Showing metabocard for Prostaglandin A2 (BMDB0002752)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:32 UTC
Update Date2020-04-22 15:11:22 UTC
BMDB IDBMDB0002752
Secondary Accession Numbers
  • BMDB02752
Metabolite Identification
Common NameProstaglandin A2
DescriptionProstaglandin A2 belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Prostaglandin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Prostaglandin a2HMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoateHMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acidHMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoateHMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acidHMDB
15(S)-Prostaglandin a2HMDB
15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylateHMDB
15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acidHMDB
15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoateHMDB
15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acidHMDB
(5E)-7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoateGenerator
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5E)-7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid
Traditional Name(+)-prostaglandin A2
CAS Registry Number13345-50-1
SMILES
CCCCC[C@H](O)\C=C\C1C=CC(=O)C1C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4+,14-12+/t16?,17-,18?/m0/s1
InChI KeyMYHXHCUNDDAEOZ-BMVCOECRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • 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
logP4.08ALOGPS
logP4.38ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.09 m³·mol⁻¹ChemAxon
Polarizability38.93 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-067r-6493000000-184e71384b97ef765979View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0209-9313300000-440ddaf4dbe3670c7d28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0169000000-4a6959ca7f335a56a955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ds-2192000000-968406dd4fa1c79a13d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l0j-9120000000-e81768601579df6c0fa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-17f7af2365a9dd00dcd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2159000000-8d1a3849012ce3208fc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9430000000-900235c5f007a38c2e53View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833602
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceGrieco, Paul A.; Abood, Norman. Facile retro Diels-Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2. Journal of the Chemical Society, Chemical Communications (1990), (5), 410-12.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available