ID: ALA4063636

Max Phase: Preclinical

Molecular Formula: C25H20FN5O3

Molecular Weight: 457.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC(=O)C(=O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1ccc(-c2ccc(F)cc2)n1

Standard InChI:  InChI=1S/C25H20FN5O3/c26-18-10-8-17(9-11-18)20-12-14-31(30-20)24-19(7-4-13-28-24)25(34)29-21(22(32)23(27)33)15-16-5-2-1-3-6-16/h1-14,21H,15H2,(H2,27,33)(H,29,34)

Standard InChI Key:  CJFKGISBMQMNDQ-UHFFFAOYSA-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: 457.47

Molecular Weight (Monoisotopic): 457.1550

AlogP: 2.47

#Rotatable Bonds: 8

Polar Surface Area: 119.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.24

CX Basic pKa: 1.24

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -1.29

References

1. Kling A, Jantos K, Mack H, Hornberger W, Drescher K, Nimmrich V, Relo A, Wicke K, Hutchins CW, Lao Y, Marsh K, Moeller A..  (2017)  Discovery of Novel and Highly Selective Inhibitors of Calpain for the Treatment of Alzheimer's Disease: 2-(3-Phenyl-1H-pyrazol-1-yl)-nicotinamides.,  60  (16): [PMID:28759231] [10.1021/acs.jmedchem.7b00731]

2. Kling A, Jantos K, Mack H, Hornberger W, Drescher K, Nimmrich V, Relo A, Wicke K, Hutchins CW, Lao Y, Marsh K, Moeller A..  (2017)  Discovery of Novel and Highly Selective Inhibitors of Calpain for the Treatment of Alzheimer's Disease: 2-(3-Phenyl-1H-pyrazol-1-yl)-nicotinamides.,  60  (16): [PMID:28759231] [10.1021/acs.jmedchem.7b00731]

3. Kling A, Jantos K, Mack H, Hornberger W, Backfisch G, Lao Y, Nijsen M, Rendenbach-Mueller B, Moeller A..  (2018)  Mitigating the Metabolic Liability of Carbonyl Reduction: Novel Calpain Inhibitors with P1' Extension.,  9  (3): [PMID:29541364] [10.1021/acsmedchemlett.7b00494]

4. Jantos K, Kling A, Mack H, Hornberger W, Moeller A, Nimmrich V, Lao Y, Nijsen M..  (2019)  Discovery of ABT-957: 1-Benzyl-5-oxopyrrolidine-2-carboxamides as selective calpain inhibitors with enhanced metabolic stability.,  29  (15): [PMID:31133534] [10.1016/j.bmcl.2019.05.034]

5. Robello M, Barresi E, Baglini E, Salerno S, Taliani S, Settimo FD..  (2021)  The Alpha Keto Amide Moiety as a Privileged Motif in Medicinal Chemistry: Current Insights and Emerging Opportunities.,  64  (7.0): [PMID:33764065] [10.1021/acs.jmedchem.0c01808]

Source

Source(1):

• Scientific Literature