Structure Database (LMSD)
Common Name
6-keto PGE1
Systematic Name
6,9-dioxo-11R,15S-dihydroxy-13E-prostenoic acid
Synonyms
- 6-keto Prostaglandin E1
LM ID
LMFA03010012
Formula
Exact Mass
Calculate m/z
368.21989
Sum Composition
Status
Curated
3D model of 6-keto PGE1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
6-keto PGE1 is a metabolite isolated after the incubation of PGI2 with rabbit liver microsomes.1 However, it is not produced in appreciable amounts following IV infusion of PGI2 in humans.2 6-keto PGE1 is equipotent with PGI2 as a vasodilator; in most other aspects its activity resembles PGE1.3
This information has been provided by Cayman Chemical
References
2. Wong, P.Y.K., Malik, K.U., Desiderio, D.M., et al. Hepatic metabolism of prostacyclin (PGI2) in the rabbit: Formation of a potent novel inhibitor of platelet aggregation. Biochem. Biophys. Res. Commun. 93(2), 486-494 (1980).
3. Jackson, E.K., Goodman, R.P., Fitzgerald, G.A., et al. Assessment of the extent to which exogenous prostaglandin I2 is converted to 6-keto-prostaglandin E1 in human subjects. J. Pharmacol. Exp. Ther. 221(1), 183-187 (1982).
String Representations
InChiKey (Click to copy)
ROUDCKODIMKLNO-CTBSXBMHSA-N
InChi (Click to copy)
InChI=1S/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
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(=O)O
Other Databases
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR1430
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
384.38
Topological Polar Surface Area
111.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
3.23
Molar Refractivity
98.65
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Updated at
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