Structure Database (LMSD)

Common Name
13,14-dihydro-15-keto-tetranor Prostaglandin D2
Systematic Name
9S-hydroxy-11,15-dioxo-2,3,4,5-tetranor-prostanoic acid
Synonyms
  • 3-[(1R,2R,5S)-5-hydroxy-3-oxo-2-(3-oxooctyl)cyclopentyl]propanoic acid
LM ID
LMFA03010245
Formula
C16H26O5
Exact Mass
Calculate m/z
298.178025
Sum Composition
FA 16:3;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View spectra on LIPID MAPS Standard Spectra DB
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]
Fatty Acids and Conjugates [FA01]
Carbocyclic fatty acids [FA0114]
Oxo fatty acids [FA0106]
Hydroxy fatty acids [FA0105]

Biological Context

A common metabolic pathway for several prostaglandins (PGs), including prostaglandin D2 (PGD2), involves the reduction of the double bond between C-13 and C-14 and oxidation of the hydroxyl group at C-15, producing 13,14-dihydro-15-keto PGs. The removal of four carbons at the α-terminus and oxidation of the terminal ω-carbon produces the abundant urinary metabolites, including tetranor-PGDM.1 13,14-dihydro-15-keto-tetranor PGD2 is a potential metabolite of PGD2. It would be produced from the known metabolite 13,14-dihydro-15-keto PGD2, which is a known agonist for the CRTH2/DP2 receptor.2

This information has been provided by Cayman Chemical

References

1. Song, W.L., Wang, M., Ricciotti, E., et al. Tetranor PGDM, an abundant urinary metabolite reflects biosynthesis of prostaglandin D2 in mice and humans. The Journal of Biological Chemisty 283(2), 1179-1188 (2008).
2. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
unidentified (#32644)
Theoretical Metabolite of PGD2

String Representations

InChiKey (Click to copy)
CIXGXJHOQWHINC-NFAWXSAZSA-N
InChi (Click to copy)
InChI=1S/C16H26O5/c1-2-3-4-5-11(17)6-7-12-13(8-9-16(20)21)15(19)10-14(12)18/h12-13,15,19H,2-10H2,1H3,(H,20,21)/t12-,13-,15+/m1/s1
SMILES (Click to copy)
[C@H]1(CCC(=O)CCCCC)C(=O)C[C@H](O)[C@@H]1CCC(=O)O

Other Databases

CHEBI ID
193578
PubChem CID
44600450
Cayman ID
13100

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings
Rotatable Bonds 10
Van der Waals Molecular Volume 309.03
Topological Polar Surface Area 91.67
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 2.63
Molar Refractivity 78.38

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Created at
21st Nov 2024
Updated at
21st Nov 2024