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Human Metabolome Database Version 2.5

 

Showing metabocard for 6-Ketoprostaglandin E1 (HMDB04241)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 16:01:54
Update Date 2009-05-05 20:59:55
Accession Number HMDB04241
Secondary Accession Numbers Not Available
Common Name 6-Ketoprostaglandin E1
Description 6-Ketoprostaglandin E1(6-keto PGE1) is a biologically active and stable prostacyclin (PGI2) metabolite and a substrate for Adenylate cyclase type III. 6-keto PGE1 is a potent coronary vasodilator. 6-keto PGE1 could be elevated in plasma of patients with primary thrombocythaemia. 6-keto-PGE1 has approximately four times less potent antiplatelet activity than PGI2 on a molar basis in man. The cardiovascular and plasma renin activity (PRA) changes are less prominent for 6-keto-PGE1 than PGI2. Salt loading slightly increases urinary 6-keto PGE1. 6-keto-PGE1 elicits the same biological effects as PGI2 in human platelets and in rabbit aorta and mesenteric artery, being, however, less potent. 6-keto-PGE1 dose-dependently stimulates adenylate cyclase activity in membranes of human platelets and cultured myocytes from rabbit aorta and mesenteric artery. The extent of stimulation of the enzyme by 6-keto-PGE1 is the same as elicited by PGI2, while the apparent affinity is lower than that of prostacyclin, both in platelets and in vascular smooth muscle cells. At the level of platelet membranes, 6-keto-PGE1 interacts with the binding sites labelled by PGI2. However, in platelets as well as in mesenteric artery myocytes, 6-keto-PGE1 interacts with only one class of sites as demonstrated either by binding or by adenylate cyclase studies, whereas PGI2 in the same conditions recognizes two different classes. (PMID: 3186779, 3075239, 3472253, 3912001, 3881881, 6391491) 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 signaling pathways.
Synonyms
  1. 6-Oxo-PGE1
  2. 6-oxo-prostaglandin E1
  3. 6-KPGE1
  4. 6-Keto-PGE1
  5. 6-Oxoprostaglandin E1
  6. 6-keto PGE1
  7. 6-ketoprostaglandin E1
  8. 6,9-dioxo-11R,15S-dihydroxy-13E-prostenoic acid
  9. 6,9-dioxo-11R,15S-dihydroxy-13E-prostenoate
Chemical IUPAC Name 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]-6-oxoheptanoic acid
Chemical Formula C20H32O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Prostanoids
Sub Class
  • Prostaglandins
Family
  • Mammalian Metabolite
Species
  • ketone
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 368.465
Monoisotopic Molecular Weight 368.219879
Isomeric SMILES CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O
Canonical SMILES CCCCCC(O)C=CC1C(O)CC(=O)C1CC(=O)CCCCC(O)=O
KEGG Compound ID C05962 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04241 Link Image
Metagene Link HMDB04241 Link Image
METLIN ID 7036 Link Image
PubChem Compound 5280889 Link Image
PubChem Substance 700559 Link Image
ChEBI ID 28269 Link Image
CAS Registry Number 67786-53-2
InChI Identifier InChI=1/C20H32O6/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/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1
Synthesis Reference Tanaka, T.; Hazato, A.; Bannai, K.; Okamura, N.; Sugiura, S.; Manabe, K.; Kurozumi, S.; Suzuki, M.; Noyori, R. Prostaglandin chemistry. XXIII. Short synthesis of 6-oxoprostaglandin E1 and 6-oxoprostaglandin F1a Tetrahedron Letters (1984), 25(43), 4947-50.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.176 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.02 [Predicted by ALOGPS]; 1.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References
  1. Mastacchi R, Fadda S, Tomasi V, Barnabei O: The effect of 6-keto-prostaglandin E1 on human lymphocyte cAMP levels. Prostaglandins Med. 1980 Dec;5(6):487-94. [PubMed Link Image]