Showing metabocard for 8-iso-15-keto-PGF2a (BMDB0005077)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:13 UTC
Update Date2020-04-22 15:15:18 UTC
BMDB IDBMDB0005077
Secondary Accession Numbers
  • BMDB05077
Metabolite Identification
Common Name8-iso-15-keto-PGF2a
Description8-iso-15-keto-PGF2a 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. Thus, 8-iso-15-keto-PGF2a is considered to be an eicosanoid. Based on a literature review very few articles have been published on 8-iso-15-keto-PGF2a.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-Oic acidHMDB
8-Iso-15-keto-PGF2alphaHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoateHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acidHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acid-cyclo[8S,12R]HMDB
8-Iso-15-keto-PGF2αHMDB
8-Iso-15-keto-PGF2aGenerator
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-iso-15-keto-PGF2α
CAS Registry Number191919-01-4
SMILES
CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1
InChI KeyLOLJEILMPWPILA-RLXHZABYSA-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
  • Cyclopentanol
  • Unsaturated fatty acid
  • Fatty acid
  • Enone
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP3.03ALOGPS
logP3.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.57 m³·mol⁻¹ChemAxon
Polarizability40.77 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, Positivesplash10-0570-4498000000-cc0a6152c4c014df4b6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-5100980000-6257b72a2aa9de720f36View 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-0019000000-910369cab5e253b484e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2295000000-e2c04166a9405e56f2fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9160000000-23fb78d0cc03202e3212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0009000000-e05daa9da0040142e39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-2069000000-8c098522c3791b504d19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9441000000-d1759dfb65fcc9f9b470View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-db45ea43b0b32962d543View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fri-0094000000-e560b2602cb2e45b3c66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052p-9151000000-c46a461dbc0a557352d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-e81e2e2f5abdc4bb9c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9356000000-a519ec47287e412b92edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-fb5ea9c2e3392b9c6014View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005077
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023618
KNApSAcK IDNot Available
Chemspider ID4446336
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283215
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available