PGH2   

GtoPdb Ligand ID: 4483

Synonyms: prostaglandin H2
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 75.99
Molecular weight 352.22
XLogP 4.35
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCC(C=CC1C2OOC(C1CC=CCCCC(=O)O)C2)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@@H]2OO[C@H]([C@@H]1C/C=C\CCCC(=O)O)C2)O
InChI InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI Key YIBNHAJFJUQSRA-YNNPMVKQSA-N
References
1. Bylund J, Hidestrand M, Ingelman-Sundberg M, Oliw EH. (2000)
Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides.
J. Biol. Chem., 275 (29): 21844-9. [PMID:10791960]
2. Gryglewski RJ, Bunting S, Moncada S, Flower RJ, Vane JR. (1976)
Arterial walls are protected against deposition of platelet thrombi by a substance (prostaglandin X) which they make from prostaglandin endoperoxides.
Prostaglandins, 12 (5): 685-713. [PMID:824685]
3. Hatae T, Hara S, Yokoyama C, Yabuki T, Inoue H, Ullrich V, Tanabe T. (1996)
Site-directed mutagenesis of human prostacyclin synthase: Alteration of Cys441 of the Cys-pocket, and Glu347 and Arg350 of the EXXR motif.
FEBS Lett., 389 (3): 268-72. [PMID:8766713]
4. Nilsson T, Ivanov IV, Oliw EH. (2010)
LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22.
Arch. Biochem. Biophys., 494 (1): 64-71. [PMID:19919823]