Structure Database (LMSD)
Common Name
delta-12-PGD2
Systematic Name
9S,15S-dihydroxy-11-oxo-5Z,12E-prostadienoic acid
Synonyms
- delta-12-Prostaglandin D2
LM ID
LMFA03010101
Formula
Exact Mass
Calculate m/z
352.224975
Sum Composition
Status
Curated
3D model of delta-12-PGD2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin D2 (PGD2) is one of the five primary enzymatic prostaglandins derived directly from PGH2. PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells including mast cells and basophils by a second, hematopoietic-type PGD synthase. PGD2 is chemically unstable, and its use and analysis is complicated by its short in vivo half-life. Δ12-PGD2 is one of the initial chemical decomposition products of PGD2. Δ12-PGD2 is an intermediate in the pathway leading to Δ12-PGJ2, which is a cyclopentenone prostaglandin with antimitotic and carcinogenic activities.1,2 The metabolism of Δ12-PGD2 involves addition of thiol nucleophiles, as is the case with the majority of cyclopentenone prostaglandins.3
This information has been provided by Cayman Chemical
References
1. Atsmon, J., Sweetman, B.J., Baertschi, S.W., et al. Formation of thiol conjugates of 9-deoxy-Δ9,Δ12(E)-prostaglandin D2 and Δ12(E)-prostaglandin D2. Biochemistry 29(15), 3760-3765 (1990).
2. Fukushima, M. Prostaglandin J2 - anti-tumor and anti-viral activities and the mechanisms involved. Eicosanoids 3(4), 189-199 (1990).
3. Kato, T., Fukushima, M., Kurozumi, S., et al. Antitumor activity of Δ7-prostaglandin A1 and Δ12-prostaglandin J2 in vitro and in vivo. Cancer Res. 46(7), 3538-3542 (1986).
String Representations
InChiKey (Click to copy)
OBTVQKDILGZFPY-WBYUMCMISA-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/h4,7,13,15-16,18,21-22H,2-3,5-6,8-12,14H2,1H3,(H,24,25)/b7-4-,17-13+/t15-,16+,18-/m0/s1
SMILES (Click to copy)
C1(=C/C[C@@H](O)CCCCC)\C(=O)C[C@H](O)[C@@H]\1C/C=C\CCCC(=O)O
Other Databases
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
3.97
Molar Refractivity
98.24
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Updated at
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