Structure Database (LMSD)

Common Name
15-epi-PGA1
Systematic Name
9-oxo-15R-hydroxy-10Z,13E-prostadienoic acid
Synonyms
  • 15-epi-Prostaglandin A1
LM ID
LMFA03010047
Formula
C20H32O4
Exact Mass
Calculate m/z
336.23006
Sum Composition
FA 20:4;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

15-epi Prostaglandin A1 (15-epi PGA1) is the 15(R) stereoisomer of PGA1. Prostaglandins of the A-series, including some with 15(R) stereochemistry, are natural products of gorgonian soft corals. PGA1 causes renal vasodilation, increased urine sodium excretion, and decreased arterial pressure in hypertensive patients.1 There are no published reports on the biological activity of 15-epi PGA1 at this time.

This information has been provided by Cayman Chemical

References

1. Krakoff, L.R., Vlachakis, N., Mendlowitz, M., et al. Differential effect of prostaglandin A1 in hypertensive patients with low, normal and high renin. Clin. Sci. Mol. Med. Suppl. 2, 311s-313s (1975).

String Representations

InChiKey (Click to copy)
BGKHCLZFGPIKKU-AHUSATQRSA-N
InChi (Click to copy)
InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17+,18+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@H](O)CCCCC)C=CC(=O)[C@@H]1CCCCCCC(=O)O

Other Databases

CHEBI ID
188416
LIPIDBANK ID
XPR1728
PubChem CID
5283050
Cayman ID
10070

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 366.80
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 4.57
Molar Refractivity 96.27

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Updated at
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