C108297   Click here for help

GtoPdb Ligand ID: 9180

Synonyms: Compound 52 [PMID:18226897]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: C108297 is a selective glucocorticoid receptor (GR) modulator, which attenuates obesity by reducing caloric intake and increasing lipolysis and fat oxidation. In addition, it attenuates inflammation by reduced macrophage infiltration and pro-inflammatory cytokine expression in white adipose tissue (WAT), as well as in vitro LPS-stimulated TNFα secretion in macrophage RAW 264.7 cells [2]. C108297 was originally reported as compound 52 [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 81.52
Molecular weight 553.24
XLogP 4.53
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES COCCOCC12Cc3cnn(c3C=C2CCN(C1)S(=O)(=O)c1ccc(cc1)C(C)(C)C)c1ccc(cc1)F
Isomeric SMILES COCCOC[C@@]12Cc3cnn(c3C=C2CCN(C1)S(=O)(=O)c1ccc(cc1)C(C)(C)C)c1ccc(cc1)F
InChI InChI=1S/C30H36FN3O4S/c1-29(2,3)23-5-11-27(12-6-23)39(35,36)33-14-13-24-17-28-22(18-30(24,20-33)21-38-16-15-37-4)19-32-34(28)26-9-7-25(31)8-10-26/h5-12,17,19H,13-16,18,20-21H2,1-4H3/t30-/m1/s1
InChI Key OMKDFVUMRKROMY-SSEXGKCCSA-N
References
1. Clark RD, Ray NC, Williams K, Blaney P, Ward S, Crackett PH, Hurley C, Dyke HJ, Clark DE, Lockey P et al.. (2008)
1H-Pyrazolo[3,4-g]hexahydro-isoquinolines as selective glucocorticoid receptor antagonists with high functional activity.
Bioorg. Med. Chem. Lett., 18 (4): 1312-7. [PMID:18226897]
2. van den Heuvel JK, Boon MR, van Hengel I, Peschier-van der Put E, van Beek L, van Harmelen V, van Dijk KW, Pereira AM, Hunt H, Belanoff JK et al.. (2016)
Identification of a selective glucocorticoid receptor modulator that prevents both diet-induced obesity and inflammation.
Br. J. Pharmacol., 173 (11): 1793-804. [PMID:26990179]