Structure Database (LMSD)

Common Name
PGD3
Systematic Name
9S,15S-dihydroxy-11-oxo-5Z,13E,17Z-prostatrienoic acid
Synonyms
  • Prostaglandin D3
LM ID
LMFA03010142
Formula
C20H30O5
Exact Mass
Calculate m/z
350.209325
Sum Composition
FA 20:5;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

Prostaglandin D3 (PGD3) is produced by the metabolism of EPA via the COX pathway.1 It is equipotent to PGD2 in decreasing systemic blood pressure in rats and in decreasing intraocular pressure in rabbits.2,3,4 However, it is 3-5 times more potent than PGD2 in the inhibition of ADP-induced human platelet aggregation.2

This information has been provided by Cayman Chemical

References

1. Kulkarni, P.S., and Srinivasan, B.D. Prostaglandins E3 and D3 lower intraocular pressure. Invest. Ophthalmol. Vis. Sci. 26(8), 1178-1182 (1985).
2. Kulkarni, P.S., Kaufman, P.L., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. J. Ocul. Pharmacol. 3(4), 349-356 (1987).
3. 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).
4. Goh, Y., Nakajima, M., Azuma, I., et al. Effects of prostaglandin D2 and its analogues on intraocular pressure in rabbits. Jpn. J. Ophthalmol. 32(4), 471-480 (1988).

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)
ANOICLBSJIMQTA-WXGBOJPQSA-N
InChi (Click to copy)
InChI=1S/C20H30O5/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/h3-4,6-7,12-13,15-18,21-22H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)C/C=C\CC)C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C13802
HMDB ID
HMDB0003034
CHEBI ID
34939
LIPIDBANK ID
XPR1705
PubChem CID
5282260
Cayman ID
12990

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 372.95
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.60
Molar Refractivity 98.07

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