Structure Database (LMSD)

Common Name
PGF3alpha
Systematic Name
9S,11R,15S-trihydroxy-5Z,13E,17Z-prostatrienoic acid
Synonyms
  • Prostaglandin F3alpha
LM ID
LMFA03010138
Formula
C20H32O5
Exact Mass
Calculate m/z
352.224975
Sum Composition
FA 20:4;O3
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

Prostaglandin F3α (PGF3α) is a COX product of EPA. The biosynthesis of PGF3α from EPA was demonstrated in vitro in human and rabbit ocular tissues.1 It has only 25% affinity at the ovine luteal FP receptor compared to PGF2α.2

This information has been provided by Cayman Chemical

References

1. Kulkarni, P.S., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in human and rabbit anterior uvea. Prostaglandins 31(6), 1159-1164 (1986).
2. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem. Pharmacol. 38(14), 2375-2381 (1989).

String Representations

InChiKey (Click to copy)
SAKGBZWJAIABSY-SAMSIYEGSA-N
InChi (Click to copy)
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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)C/C=C\CC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C06476
HMDB ID
HMDB0002122
CHEBI ID
36075
LIPIDBANK ID
XPR1502
PubChem CID
5280940
Cayman ID
16990

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 375.59
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.68
Molar Refractivity 99.59

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Updated at
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