4-Methyl-2-(4'-piperazin-1-yl-biphenyl-3-yl)-pentanoic acid cyanomethyl-amide

ID: ALA184514

Chembl Id: CHEMBL184514

PubChem CID: 9908450

Max Phase: Preclinical

Molecular Formula: C24H30N4O

Molecular Weight: 390.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](C(=O)NCC#N)c1cccc(-c2ccc(N3CCNCC3)cc2)c1

Standard InChI:  InChI=1S/C24H30N4O/c1-18(2)16-23(24(29)27-11-10-25)21-5-3-4-20(17-21)19-6-8-22(9-7-19)28-14-12-26-13-15-28/h3-9,17-18,23,26H,11-16H2,1-2H3,(H,27,29)/t23-/m1/s1

Standard InChI Key:  AQPCFTUFFUSBNZ-HSZRJFAPSA-N

Alternative Forms

1. Parent:

   

   ALA184514

   (2R)-N-(cyanomethyl)-4-methyl-2-{3-[4-(piperazin-1-yl)phenyl]phenyl}pentanamide

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: 390.53

Molecular Weight (Monoisotopic): 390.2420

AlogP: 3.53

#Rotatable Bonds: 7

Polar Surface Area: 68.16

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.51

CX Basic pKa: 8.88

CX LogP: 3.50

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -0.93

References

1. Robichaud J, Oballa R, Prasit P, Falgueyret JP, Percival MD, Wesolowski G, Rodan SB, Kimmel D, Johnson C, Bryant C, Venkatraman S, Setti E, Mendonca R, Palmer JT..  (2003)  A novel class of nonpeptidic biaryl inhibitors of human cathepsin K.,  46  (17): [PMID:12904076] [10.1021/jm0301078]

2. Robichaud J, Bayly C, Oballa R, Prasit P, Mellon C, Falgueyret JP, Percival MD, Wesolowski G, Rodan SB..  (2004)  Rational design of potent and selective NH-linked aryl/heteroaryl cathepsin K inhibitors.,  14  (16): [PMID:15261289] [10.1016/j.bmcl.2004.05.087]

3. Black WC, Bayly CI, Davis DE, Desmarais S, Falgueyret JP, Léger S, Li CS, Massé F, McKay DJ, Palmer JT, Percival MD, Robichaud J, Tsou N, Zamboni R..  (2005)  Trifluoroethylamines as amide isosteres in inhibitors of cathepsin K.,  15  (21): [PMID:16154747] [10.1016/j.bmcl.2005.07.071]

4. Falgueyret JP, Desmarais S, Oballa R, Black WC, Cromlish W, Khougaz K, Lamontagne S, Massé F, Riendeau D, Toulmond S, Percival MD..  (2005)  Lysosomotropism of basic cathepsin K inhibitors contributes to increased cellular potencies against off-target cathepsins and reduced functional selectivity.,  48  (24): [PMID:16302795] [10.1021/jm0504961]

5. Setti EL, Venkatraman S, Palmer JT, Xie X, Cheung H, Yu W, Wesolowski G, Robichaud J..  (2006)  Design and synthesis of tetracyclic nonpeptidic biaryl nitrile inhibitors of cathepsin K.,  16  (16): [PMID:16750630] [10.1016/j.bmcl.2006.05.061]

Source

Source(1):

• Scientific Literature