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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:09 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002776
Secondary Accession Numbers
  • HMDB0011650
  • HMDB02776
  • HMDB11650
Metabolite Identification
Common Name13,14-Dihydro-15-keto-PGE2
Description
Structure
Thumb
Synonyms
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional NamePGEM
CAS Registry Number363-23-5
SMILES
CCCCCC(=O)CC[C@H]1[C@H](O)CC(=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/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1
InChI KeyCUJMXIQZWPZMNQ-XYYGWQPLSA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000224 +/- 0.000057 uMAdult (>18 years old)BothSchizophrenia details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Mathe AA, Eberhard G, Saaf J, Wetterberg L: Plasma prostaglandin E2 metabolite--measured as 11-deoxy-15-keto-13,14-dihydro-11 beta,16 xi-cyclo-PGE2--in twins with schizophrenic disorder. Biol Psychiatry. 1986 Sep;21(11):1024-30. [PubMed:3741918 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023063
KNApSAcK IDNot Available
Chemspider ID4444296
KEGG Compound IDC04671
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2311
PubChem Compound5280711
PDB IDNot Available
ChEBI ID15550
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]
  2. Gordon-Wright AP, Elder MG: Effect of prostaglandin E2 and its metabolites on lower segment myometrium in vitro. Eur J Obstet Gynecol Reprod Biol. 1980 Jun;10(5):297-302. [PubMed:7190512 ]
  3. Hume R, Bell J, Cossar D, Giles M, Hallas A, Kelly R: Differential release of prostaglandins by organ cultures of human fetal trachea and lung. In Vitro Cell Dev Biol Anim. 1996 Jan;32(1):24-9. [PubMed:8835315 ]