ID: ALA3358151

Max Phase: Preclinical

Molecular Formula: C13H14ClN3O4

Molecular Weight: 311.73

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@]1(CNC(=O)COc2ccc(Cl)cc2)NC(=O)NC1=O

Standard InChI:  InChI=1S/C13H14ClN3O4/c1-13(11(19)16-12(20)17-13)7-15-10(18)6-21-9-4-2-8(14)3-5-9/h2-5H,6-7H2,1H3,(H,15,18)(H2,16,17,19,20)/t13-/m1/s1

Standard InChI Key:  LNIRXDCIYOBRPL-CYBMUJFWSA-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: 311.73

Molecular Weight (Monoisotopic): 311.0673

AlogP: 0.43

#Rotatable Bonds: 5

Polar Surface Area: 96.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.89

CX Basic pKa:

CX LogP: 0.34

CX LogD: 0.32

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -1.32

References

1. Durham TB, Klimkowski VJ, Rito CJ, Marimuthu J, Toth JL, Liu C, Durbin JD, Stout SL, Adams L, Swearingen C, Lin C, Chambers MG, Thirunavukkarasu K, Wiley MR..  (2014)  Identification of potent and selective hydantoin inhibitors of aggrecanase-1 and aggrecanase-2 that are efficacious in both chemical and surgical models of osteoarthritis.,  57  (24): [PMID:25415648] [10.1021/jm501522n]

2. Durham TB, Marimuthu J, Toth JL, Liu C, Adams L, Mudra DR, Swearingen C, Lin C, Chambers MG, Thirunavukkarasu K, Wiley MR..  (2017)  A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose.,  60  (13): [PMID:28613895] [10.1021/acs.jmedchem.7b00650]

Source

Source(1):

• Scientific Literature