Structure Database (LMSD)

Common Name
ent-15-F2t-IsoP
Systematic Name
9R,11S,15R-trihydroxy-5Z,13E-prostadienoic acid-cyclo[8R,12S]
Synonyms
  • (9R,11S,15R)-15-F2-IsoP[8R,12S]
LM ID
LMFA03110031
Formula
C20H34O5
Exact Mass
Calculate m/z
354.240625
Sum Composition
FA 20:3;O3
Status
Computationally Generated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Isoprostanes [FA0311]

Biological Context

Isoprostanes are produced by the non-enzymatic, free radical peroxidation of arachidonic acid. They have been used as biomarkers of oxidative stress, but also have been found to have a potent biological activity. ent-8-iso Prostaglandin F2α (ent-8-iso PGF2α) is a potent vasoconstrictor of porcine retinal and brain microvessels with EC50 values of 31 and 54 nM, respectively.1

This information has been provided by Cayman Chemical

References

1. Hou, X., Robers, L.J., II, Gobeil, F., Jr., et al. Isomer-specific contractile effects of a series of synthetic F2-isoprostanes on retinal and cerebral microvasculature. Free Radic. Biol. Med. 36(2), 163-172 (2004).

String Representations

InChiKey (Click to copy)
PXGPLTODNUVGFL-VCKDCIDJSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m1/s1
SMILES (Click to copy)
C(CCC/C=C\C[C@@H]1[C@H](/C=C/[C@H](O)CCCCC)[C@@H](O)C[C@H]1O)(=O)O

Other Databases

PubChem CID
40768305
Cayman ID
10011545

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 378.23
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.90
Molar Refractivity 99.68

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Created at
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Updated at
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