Structure Database (LMSD)

Common Name
PGD2
Systematic Name
9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoic acid
Synonyms
  • Prostaglandin D2
  • 11-Dehydroprostaglandin F2-alpha
  • 11-Dehydroprostaglandin F2alpha
  • (5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate
LM ID
LMFA03010004
Formula
Exact Mass
Calculate m/z
352.224975
Sum Composition
Status
Curated



Classification

Biological Context

Prostaglandin D2 (PGD2) is the major eicosanoid product of mast cells and is released in large quantities during allergic and asthmatic anaphylaxis.1 Mastocytosis patients produce excessive amounts of PGD2, which causes vasodilation, flushing, hypotension, and syncopal episodes.1 PGD2 is also produced in the brain via an alternative pathway involving a soluble, secreted PGD-synthase also known as β-trace.2,3 In the brain, PGD2 produces normal physiological sleep and lowering of body temperature.2,3 Further pharmacological actions include inhibition of platelet aggregation and relaxation of vascular smooth muscle.4 PGD2 inhibits human ovarian tumor cell proliferation with an IC50 of 6.8 µM.5

This information has been provided by Cayman Chemical

References

1. Kikuchi, Y., Kita, T., Hirata, J., et al. Preclinical studies of antitumor prostaglandins by using human ovarian cancer cells. Cancer Metastasis Rev. 13(3-4), 309-315 (1994).
4. Roberts, L.J., II, and Sweetman, B.J. Metabolic fate of endogenously synthesized prostaglandin D2 in a human female with mastocytosis. Prostaglandins 30(3), 383-400 (1985).
5. Hayaishi, O. Sleep-wake regulation by prostaglandins D2 and E2. J. Biol. Chem. 263(29), 14593-14596 (1988).

Reactions

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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)
BHMBVRSPMRCCGG-OUTUXVNYSA-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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR1301
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

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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