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Structure Database (LMSD)

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Common Name

15-methyl-15S-PGD2

Systematic Name

9S,15S-dihydroxy-11-oxo-15-methyl-5Z,13E-prostadienoic acid

Synonyms

15-methyl-15S-Prostaglandin D2

LM ID

LMFA03010050

Formula

C₂₁H₃₄O₅

Exact Mass

Calculate m/z

366.240625

Sum Composition

FA 21:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(S)-15-methyl Prostaglandin D2 (15(S)-15-methyl PGD2) is a metabolically stable synthetic analog of PGD2 . In contrast to PGD2, 15(S)-15-methyl PGD2 induces vasoconstriction and increases systemic blood pressure with much reduced inhibitory activity on ADP-induced platelet aggregation.¹ It also exhibits strong antifertility activity in hamsters (200-fold more potent than PGD2).¹

This information has been provided by Cayman Chemical

References

1. Bundy, G.L., Morton, D.R., Peterson, D.C., et al. Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues. J. Med. Chem. 26(6), 790-799 (1983).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues.,
J Med Chem, 1983

Pubmed ID: 6854581

String Representations

InChiKey (Click to copy)

CTXLUMAOXBULOZ-QEQARHSSSA-N

InChi (Click to copy)

InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-18,22,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,21+/m1/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@](C)(O)CCCCC)C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O