Structure Database (LMSD)

Common Name
PGD2-d9
Systematic Name
9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoic-17,17,18,18,19,19,20,20,20-d9 acid
Synonyms
  • Prostaglandin D2-d9
  • 11-Dehydroprostaglandin F2-alpha-d9
  • 11-Dehydroprostaglandin F2alpha-d9
  • 9alpha,15S-dihydroxy-11-oxo-prosta-5Z,13E-dien-1-oic-17,17,18,18,19,19,20,20,20-d9 acid
LM ID
LMFA03010256
Formula
Exact Mass
Calculate m/z
361.281466
Status
Curated

Classification

Biological Context

Prostaglandin D2-d9 (PGD2-d9) is intended for use as an internal standard for the quantification of PGD2 by GC- or LC-MS. 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 value of 6.8 µM.5

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
BHMBVRSPMRCCGG-UVUOTMQPSA-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/i1D3,2D2,3D2,6D2
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings
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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Created at
15th May 2025
Updated at
15th May 2025