2-(N-methyl-N-phenylamino)-N-((5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl)acetamide

ID: ALA4859268

Chembl Id: CHEMBL4859268

Cas Number: 920289-29-8

PubChem CID: 16048422

Max Phase: Phase

Molecular Formula: C28H29FN2O4

Molecular Weight: 476.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Agg-523 | PF-05212371 | PF-5212371 | WAY-266523 | AGG-523|920289-29-8|UNII-WO23I2827Q|WAY-266523|WO23I2827Q|PF-5212371|PF-05212371|Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-|CHEMBL4859268|4-(S)-(((Biphenyl-4-yl)carbonyl)amino)-4-((2-(4-fluorophenyl)-1,1-dimethylethyl)carbamoyl)butyric acid|(4S)-5-[[1-(4-fluorophenyl)-2-methylpropan-2-yl]amino]-5-oxo-4-[(4-phenylbenzoyl)amino]pentanoic acid|SCHEMBL2245079|JWQMTWCFNZSLNR-DEShow More⌵

Canonical SMILES:  CC(C)(Cc1ccc(F)cc1)NC(=O)[C@H](CCC(=O)O)NC(=O)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C28H29FN2O4/c1-28(2,18-19-8-14-23(29)15-9-19)31-27(35)24(16-17-25(32)33)30-26(34)22-12-10-21(11-13-22)20-6-4-3-5-7-20/h3-15,24H,16-18H2,1-2H3,(H,30,34)(H,31,35)(H,32,33)/t24-/m0/s1

Standard InChI Key:  JWQMTWCFNZSLNR-DEOSSOPVSA-N

Alternative Forms

1. Parent:

   

   ALA4859268

   AGG-523

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.55

Molecular Weight (Monoisotopic): 476.2111

AlogP: 4.59

#Rotatable Bonds: 10

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.25

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.40

Np Likeness Score: -0.60

References

1. Gilbert AM, Bursavich MG, Lombardi S, Georgiadis KE, Reifenberg E, Flannery CR, Morris EA..  (2008)  N-((8-hydroxy-5-substituted-quinolin-7-yl)(phenyl)methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2).,  18  (24): [PMID:18974001] [10.1016/j.bmcl.2008.10.065]

2. Unpublished dataset, 

3. Brebion F, Gosmini R, Deprez P, Varin M, Peixoto C, Alvey L, Jary H, Bienvenu N, Triballeau N, Blanque R, Cottereaux C, Christophe T, Vandervoort N, Mollat P, Touitou R, Leonard P, De Ceuninck F, Botez I, Monjardet A, van der Aar E, Amantini D..  (2021)  Discovery of GLPG1972/S201086, a Potent, Selective, and Orally Bioavailable ADAMTS-5 Inhibitor for the Treatment of Osteoarthritis.,  64  (6.0): [PMID:33719441] [10.1021/acs.jmedchem.0c02008]

4. Cuffaro D, Ciccone L, Rossello A, Nuti E, Santamaria S..  (2022)  Targeting Aggrecanases for Osteoarthritis Therapy: From Zinc Chelation to Exosite Inhibition.,  65  (20.0): [PMID:36250680] [10.1021/acs.jmedchem.2c01177]

Source

Source(2):

• Scientific Literature
• Clinical Candidates