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Structure Database (LMSD)

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Common Name

13,14-dihydro-15-keto-PGD2

Systematic Name

11,15-dioxo-9S-hydroxy-5Z-prostenoic acid

Synonyms

13,14-dihydro-15-keto-Prostaglandin D2
dhk-PGD2

LM ID

LMFA03010022

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

Biological Context

13,14-dihydro-15-keto Prostaglandin D2 (13,14-dihydro-15-keto PGD2) is a metabolite of PGD2 which is formed through the 15-hydroxy PGDH pathway. 13,14-dihydro-15-keto PGD2 was recently identified as a selective agonist for the CRTH2/DP2 receptor.¹ It also inhibits ion flux in a canine colonic mucosa preparation.² In humans, 13,14-dihydro-15-keto PGD2 is further metabolized to give 11β-hydroxy compounds which have also undergone β-oxidation of one or both side chains. Virtually no 13,14-dihydro-15-keto PGD2 survives intact in the urine.^3,4

This information has been provided by Cayman Chemical

References

1. Morrow, J.D., Prakash, C., Awad, J.A., et al. Quantification of the major urinary metabolite of prostaglandin D2 by a stable isotope dilution mass spectrometric assay. Anal. Biochem. 193(1), 142-148 (1991).

2. Liston, T.E., and Roberts, L.J., II Metabolic fate of radiolabeled prostaglandin D2 in a normal human male volunteer. The Journal of Biological Chemisty 260(24), 13172-13180 (1985).

3. Rangachari, P.K., and Betti, P.A. Biological activity of metabolites of PGD2 on canine proximal colon. Am. J. Physiol. 264(5 Pt 1), G886-G894 (1993).

4. Hirai, H., Tanaka, K., Yoshie, O., et al. Prostaglandin D2 selectivity induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2. J. Exp. Med. 193(2), 255-261 (2001).

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

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

VSRXYLYXIXYEST-KZTWKYQFSA-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/h4,7,16-18,22H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+/m1/s1

SMILES (Click to copy)

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