Structure Database (LMSD)

Common Name
19R-hydroxy-PGF2alpha
Systematic Name
9S,11R,15S,19R-tetrahydroxy-5Z,13E-prostadienoic acid
Synonyms
  • 19(R)-hydroxy-Prostaglandin F2alpha
LM ID
LMFA03010042
Formula
C20H34O6
Exact Mass
Calculate m/z
370.23554
Sum Composition
FA 20:3;O4
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

19(R)-hydroxy PGF2α is an ω-1 hydroxylase metabolite of PGF2α found in human semen. The concentration of 19(R)-hydroxy PGF compounds (F2α and F1α together) in fresh human semen is about 20 µg/ml.1 19(R)-hydroxy PGF2α exhibits no activity at the FP receptor of the cat iris sphincter muscle at concentrations up to 1 µM.2

This information has been provided by Cayman Chemical

References

1. Taylor, P.L., and Kelly, R.W. The occurrence of 19-hydroxy F prostaglandins in human semen. FEBS Lett. 57(1), 22-25 (1975).
2. Woodward, D.F., Protzman, C.E., Krauss, A.H.P., et al. Identification of 19(R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist. Prostaglandins 46(4), 371-383 (1993).

String Representations

InChiKey (Click to copy)
UBWZMPMLSDJDSU-OQRQNLQMSA-N
InChi (Click to copy)
InChI=1S/C20H34O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-19,21-24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,18+,19-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCC[C@H](O)C)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

CHEBI ID
165315
LIPIDBANK ID
XPR1722
PubChem CID
5283047
Cayman ID
16910

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 387.02
Topological Polar Surface Area 118.22
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 6
logP 3.16
Molar Refractivity 101.58

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Updated at
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