compound 3 [PMID: 21650226]   Click here for help

GtoPdb Ligand ID: 8745

Compound class: Synthetic organic
Comment: Compound 3 is reported as a thiazolidinedione analogue inhibitor of 15-hydroxyprostaglandin dehydrogenase (HPGD) [2]. This compound is also example 11 in patent US8637558 B2, which describes its use for the prevention or treatment of cardiovascular disease, gastrointestinal disease, renal disease and other conditions by increasing prostaglandin levels via inhibition of HPGD-induced prostaglandin metabolism [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 80.7
Molecular weight 365.09
XLogP 5.23
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C1NC(=O)C(=Cc2ccc(c(c2)Cl)OCCC2CCCCC2)S1
Isomeric SMILES O=C1NC(=O)/C(=C/c2ccc(c(c2)Cl)OCCC2CCCCC2)/S1
InChI InChI=1S/C18H20ClNO3S/c19-14-10-13(11-16-17(21)20-18(22)24-16)6-7-15(14)23-9-8-12-4-2-1-3-5-12/h6-7,10-12H,1-5,8-9H2,(H,20,21,22)/b16-11-
InChI Key DBBGLVJTGXKCHY-WJDWOHSUSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(5Z)-5-[[3-chloro-4-(2-cyclohexylethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
Database Links Click here for help
ChEMBL Ligand CHEMBL1800139
GtoPdb PubChem SID 252827403
PubChem CID 46836953
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