compound 23 [PMID: 35944849]   Click here for help

GtoPdb Ligand ID: 12208

Compound class: Synthetic organic
Comment: Compound 23 is a selective cathepsin K inhibitor [2]. Cathepsin K (a collagenase) is upregulated in osteoclasts, chondrocytes and synoviocytes in osteoarthritic (OA) diseases, so inhibiting this cysteine protease would be expected to reduce/delay cartilage/subchondral bone destruction in OA joints [1]. Compound 23 is active in vitro and target engagement has been demonstrated in vivo.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 124.68
Molecular weight 562.66
XLogP 4.67
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES N#CC1(CC1)NC(=O)[C@@H]1CCCC[C@H]1c1oc(nc1c1ccc(cc1)N1CCS(=O)(=O)CC1)c1ccc(cc1)F
Isomeric SMILES Fc1ccc(cc1)c1nc(c(o1)[C@@H]1CCCC[C@H]1C(=O)NC1(CC1)C#N)c1ccc(cc1)N1CCS(=O)(=O)CC1
InChI InChI=1S/C30H31FN4O4S/c31-22-9-5-21(6-10-22)29-33-26(20-7-11-23(12-8-20)35-15-17-40(37,38)18-16-35)27(39-29)24-3-1-2-4-25(24)28(36)34-30(19-32)13-14-30/h5-12,24-25H,1-4,13-18H2,(H,34,36)/t24-,25-/m1/s1
InChI Key SBWFYUHMCHTQJT-JWQCQUIFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1R,2R)-N-(1-cyanocyclopropyl)-2-[4-[4-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]-2-(4-fluorophenyl)-1,3-oxazol-5-yl]cyclohexane-1-carboxamide
Database Links Click here for help
GtoPdb PubChem SID 472319328
PubChem CID 117993213
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