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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:17 UTC
Update Date2021-09-14 15:47:03 UTC
HMDB IDHMDB0002886
Secondary Accession Numbers
  • HMDB02886
Metabolite Identification
Common Name6-Keto-prostaglandin F1a
Description6-keto-Prostaglandin F1a is the physiologically active and stable metabolite of prostacyclin. (A prostaglandin found in nearly all mammalian tissue that is a powerful vasodilator and inhibits platelet aggregation; it is biosynthesized enzymatically from prostaglandin endoperoxides in human vascular tissue; the sodium salt has been also used to treat primary pulmonary hypertension (Hypertension, Pulmonary). A delayed and prolonged increase in 6-keto-PGF1 alpha is reported in animals with septic shock, i.e., those with fecal peritonitis or cecal ligation. 6-keto-Prostaglandin F1a plasma levels has been found increased in patients with epidemic hemorrhagic fever, in patients with acute obstructive suppurative cholangitis, in patients with gynecologic cancer and has significant correlation with the level of high density lipoprotein cholesterol in plasma. (PMID 1976492 , 2298410 , 2379443 , 2111556 )Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Data?1582752258
Synonyms
Chemical FormulaC20H34O6
Average Molecular Weight370.4804
Monoisotopic Molecular Weight370.23553882
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
Traditional Name6 keto PGF1 α
CAS Registry Number58962-34-8
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1
InChI KeyKFGOFTHODYBSGM-ZUNNJUQCSA-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
  • Fatty alcohol
  • Hydroxy fatty acid
  • Keto fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available196.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00001910
[M+H]+Not Available179.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00001910
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adipose Tissue
  • Kidney
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Cardiopulmonary resuscitation
  1. Strohmenger HU, Lindner KH, Keller A, Lindner IM, Bothner U, Georgieff M: Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55. [PubMed:7634804 ]
Hydrocephalus
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Ischemia
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Meningitis
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Rheumatoid arthritis
  1. Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6. [PubMed:6589104 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023077
KNApSAcK IDNot Available
Chemspider ID4444411
KEGG Compound IDC05961
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6782
PubChem Compound5280888
PDB IDNot Available
ChEBI ID28158
Food Biomarker OntologyNot Available
VMH IDCE0955
MarkerDB IDMDB00000405
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References