ID: ALA2163587

Max Phase: Preclinical

Molecular Formula: C24H28N4O3

Molecular Weight: 420.51

Molecule Type: Small molecule

Representations

Synonyms (1): AZD-4996
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cccc2c3c([nH]c12)CCN(C(=O)[C@@H]1CCCC[C@H]1C(=O)NC1(C#N)CC1)C3

Standard InChI:  InChI=1S/C24H28N4O3/c1-31-20-8-4-7-15-18-13-28(12-9-19(18)26-21(15)20)23(30)17-6-3-2-5-16(17)22(29)27-24(14-25)10-11-24/h4,7-8,16-17,26H,2-3,5-6,9-13H2,1H3,(H,27,29)/t16-,17-/m1/s1

Standard InChI Key:  ZJIQEAXGKFPTII-IAGOWNOFSA-N

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

Properties

Molecular Weight: 420.51

Molecular Weight (Monoisotopic): 420.2161

AlogP: 3.04

#Rotatable Bonds: 4

Polar Surface Area: 98.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.89

CX Basic pKa:

CX LogP: 1.80

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.79

Np Likeness Score: -0.99

References

1. Dossetter AG, Beeley H, Bowyer J, Cook CR, Crawford JJ, Finlayson JE, Heron NM, Heyes C, Highton AJ, Hudson JA, Jestel A, Kenny PW, Krapp S, Martin S, MacFaul PA, McGuire TM, Gutierrez PM, Morley AD, Morris JJ, Page KM, Ribeiro LR, Sawney H, Steinbacher S, Smith C, Vickers M..  (2012)  (1R,2R)-N-(1-cyanocyclopropyl)-2-(6-methoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexanecarboxamide (AZD4996): a potent and highly selective cathepsin K inhibitor for the treatment of osteoarthritis.,  55  (14): [PMID:22742641] [10.1021/jm3007257]

2. Crawford JJ, Kenny PW, Bowyer J, Cook CR, Finlayson JE, Heyes C, Highton AJ, Hudson JA, Jestel A, Krapp S, Martin S, Macfaul PA, McDermott BP, McGuire TM, Morley AD, Morris JJ, Page KM, Ribeiro LR, Sawney H, Steinbacher S, Smith C, Dossetter AG..  (2012)  Pharmacokinetic benefits of 3,4-dimethoxy substitution of a phenyl ring and design of isosteres yielding orally available cathepsin K inhibitors.,  55  (20): [PMID:22984809] [10.1021/jm301119s]

Source

Source(1):

• Scientific Literature