Structure Database (LMSD)

Common Name
15-keto-PGF2alpha
Systematic Name
9S,11R-dihydroxy-15-oxo-5Z,13E-prostadienoic acid
Synonyms
  • 15-keto-Prostaglandin F2alpha
  • 15k-PGF2a
LM ID
LMFA03010026
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
View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

15-keto Prostaglandin F2α (15-keto PGF2α) is the first metabolite of PGF2α. in the 15-hydroxy PGDH pathway. It is one of the critical components in the goldfish and Atlantic salmon postovulatory pheromone.1,2 15-keto PGF2α stimulates the male goldfish and salmon olfactory receptors with detection thresholds of 10-12 and 10-8 M, respectively.1,2 15-keto PGF2α is 10-fold less active than PGF2α in decreasing rabbit intraocular pressure.3

This information has been provided by Cayman Chemical

References

1. Moore, A., and Waring, C.P. Electrophysiological and endocrinological evidence that F-series prostaglandins function as priming pheromones in mature male Atlantic salmon (Salmo salar) PARR. J. Exp. Biol. 199(Pt 10), 2307-2316 (1996).
2. Woodward, D.F., Williams, L.S., and Chen, J. Marked differential effects of prostanoid metabolites on rabbit intraocular pressure. Ophthalmic Res. 21(6), 428-435 (1989).
3. Sorensen, P.W., Hara, T.J., Goetz, F.W., et al. F prostaglandins function as potent olfactory stimulants that comprise the postovulatory female sex pheromone in goldfish. Biol. Reprod. 39(5), 1039-1050 (1988).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
LOLJEILMPWPILA-AMFHKTBMSA-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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,18+,19-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/C(=O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C05960
HMDB ID
HMDB0004240
CHEBI ID
28442
LIPIDBANK ID
XPR1511
PubChem CID
5280887
Cayman ID
16720

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 375.59
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.82
Molar Refractivity 98.17

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Updated at
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