(1R,2R)-5,5-Dichloro-N-(1-cyanocyclopropyl)-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexanecarboxamide

ID: ALA523352

Chembl Id: CHEMBL523352

PubChem CID: 11990595

Max Phase: Preclinical

Molecular Formula: C23H23Cl2F3N4O3S

Molecular Weight: 563.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MK-1256 | CHEMBL523352|MK-1256|(1R,2R)-5,5-Dichloro-N-(1-cyanocyclopropyl)-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexanecarboxamide|(1R,2R)-5,5-dichloro-N-(1-cyanocyclopropyl)-2-(4-(4-(methylsulfonyl)phenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)cyclohexanecarboxamide|SCHEMBL1624397|DSHIORGRZXPVSN-IAGOWNOFSA-N|BDBM50253098|(1R,2R)-5,5-dichloro-N-(1-cyanocyclopropyl)-2-[4-(4-methylsulfonylphenyl)-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexane-1-carboxamShow More⌵

Canonical SMILES:  CS(=O)(=O)c1ccc(-c2cn(CC(F)(F)F)nc2[C@@H]2CCC(Cl)(Cl)C[C@H]2C(=O)NC2(C#N)CC2)cc1

Standard InChI:  InChI=1S/C23H23Cl2F3N4O3S/c1-36(34,35)15-4-2-14(3-5-15)18-11-32(13-23(26,27)28)31-19(18)16-6-7-22(24,25)10-17(16)20(33)30-21(12-29)8-9-21/h2-5,11,16-17H,6-10,13H2,1H3,(H,30,33)/t16-,17-/m1/s1

Standard InChI Key:  DSHIORGRZXPVSN-IAGOWNOFSA-N

Alternative Forms

1. Parent:

   

   ALA523352

   (1R,2R)-5,5-Dichloro-N-(1-cyanocyclopropyl)-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexanecarboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 563.43

Molecular Weight (Monoisotopic): 562.0820

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 104.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.40

CX Basic pKa: 1.16

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.51

Np Likeness Score: -0.95

References

1. Robichaud J, Black WC, Thérien M, Paquet J, Oballa RM, Bayly CI, McKay DJ, Wang Q, Isabel E, Léger S, Mellon C, Kimmel DB, Wesolowski G, Percival MD, Massé F, Desmarais S, Falgueyret JP, Crane SN..  (2008)  Identification of a nonbasic, nitrile-containing cathepsin K inhibitor (MK-1256) that is efficacious in a monkey model of osteoporosis.,  51  (20): [PMID:18811135] [10.1021/jm800610j]

2. Allen JG, Fotsch C, Babij P..  (2010)  Emerging targets in osteoporosis disease modification.,  53  (11): [PMID:20218623] [10.1021/jm9018756]

3. Ginnetti AT, Paone DV, Nanda KK, Li J, Busuek M, Johnson SA, Lu J, Soisson SM, Robinson R, Fisher J, Webber A, Wesolowski G, Ma B, Duong L, Carroll S, Burgey CS, Stachel SJ..  (2022)  Lead optimization of cathepsin K inhibitors for the treatment of Osteoarthritis.,  74  [PMID:35944849] [10.1016/j.bmcl.2022.128927]

Source

Source(1):

• Scientific Literature