ID: ALA3261926

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  N#Cc1ccc(-c2ccc(C[C@@H](C#N)NC(=O)C3(N)CCOCC3)cc2)cc1

Standard InChI:  InChI=1S/C22H22N4O2/c23-14-17-3-7-19(8-4-17)18-5-1-16(2-6-18)13-20(15-24)26-21(27)22(25)9-11-28-12-10-22/h1-8,20H,9-13,25H2,(H,26,27)/t20-/m0/s1

Standard InChI Key:  NNUFRZJZOXVZIT-FQEVSTJZSA-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: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 2.28

#Rotatable Bonds: 5

Polar Surface Area: 111.93

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.90

CX Basic pKa: 8.61

CX LogP: 1.72

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.83

Np Likeness Score: -0.59

References

1. Furber M, Tiden AK, Gardiner P, Mete A, Ford R, Millichip I, Stein L, Mather A, Kinchin E, Luckhurst C, Barber S, Cage P, Sanganee H, Austin R, Chohan K, Beri R, Thong B, Wallace A, Oreffo V, Hutchinson R, Harper S, Debreczeni J, Breed J, Wissler L, Edman K..  (2014)  Cathepsin C inhibitors: property optimization and identification of a clinical candidate.,  57  (6): [PMID:24592859] [10.1021/jm401705g]

2. Doyle K, Lönn H, Käck H, Van de Poël A, Swallow S, Gardiner P, Connolly S, Root J, Wikell C, Dahl G, Stenvall K, Johannesson P..  (2016)  Discovery of Second Generation Reversible Covalent DPP1 Inhibitors Leading to an Oxazepane Amidoacetonitrile Based Clinical Candidate (AZD7986).,  59  (20): [PMID:27690432] [10.1021/acs.jmedchem.6b01127]

3. Hou W, Sun H, Ma Y, Liu C, Zhang Z..  (2019)  Identification and Optimization of Novel Cathepsin C Inhibitors Derived from EGFR Inhibitors.,  62  (12): [PMID:31145622] [10.1021/acs.jmedchem.9b00631]

4. Banerjee A, Velagaleti R, Patil S, Pawar M, Yadav P, Kadam P, Qadri MM, Chakraborti S, Saini JS, Behera DB, Karanjai K, Iyer PS, Gharat LA, Das S..  (2021)  Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy.,  47  [PMID:34139325] [10.1016/j.bmcl.2021.128202]

Source

Source(1):

• Scientific Literature