ID: ALA3358158

Max Phase: Preclinical

Molecular Formula: C18H14F3N5O4

Molecular Weight: 421.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cn1ccnc1[C@]1(CNC(=O)c2cc3cc(C(F)(F)F)ccc3o2)NC(=O)NC1=O

Standard InChI:  InChI=1S/C18H14F3N5O4/c1-26-5-4-22-14(26)17(15(28)24-16(29)25-17)8-23-13(27)12-7-9-6-10(18(19,20)21)2-3-11(9)30-12/h2-7H,8H2,1H3,(H,23,27)(H2,24,25,28,29)/t17-/m0/s1

Standard InChI Key:  PDBQNZHFRVAZBC-KRWDZBQOSA-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: 421.34

Molecular Weight (Monoisotopic): 421.0998

AlogP: 1.65

#Rotatable Bonds: 4

Polar Surface Area: 118.26

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.48

CX Basic pKa: 5.43

CX LogP: 0.88

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -1.20

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. Wiley MR, Durham TB, Adams LA, Chambers MG, Lin C, Liu C, Marimuthu J, Mitchell PG, Mudra DR, Swearingen CA, Toth JL, Weller JM, Thirunavukkarasu K..  (2016)  Use of Osmotic Pumps to Establish the Pharmacokinetic-Pharmacodynamic Relationship and Define Desirable Human Performance Characteristics for Aggrecanase Inhibitors.,  59  (12): [PMID:27194201] [10.1021/acs.jmedchem.6b00398]

Source

Source(1):

• Scientific Literature