ID: ALA402393

Max Phase: Preclinical

Molecular Formula: C22H21F3N4O4

Molecular Weight: 462.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(N[C@@H]1CCOC[C@@H]1C(=O)NO)c1ccc(Cc2c(C(F)(F)F)nn3ccccc23)cc1

Standard InChI:  InChI=1S/C22H21F3N4O4/c23-22(24,25)19-15(18-3-1-2-9-29(18)27-19)11-13-4-6-14(7-5-13)20(30)26-17-8-10-33-12-16(17)21(31)28-32/h1-7,9,16-17,32H,8,10-12H2,(H,26,30)(H,28,31)/t16-,17+/m0/s1

Standard InChI Key:  SXDMGWZDRWQMPS-DLBZAZTESA-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: 462.43

Molecular Weight (Monoisotopic): 462.1515

AlogP: 2.58

#Rotatable Bonds: 5

Polar Surface Area: 104.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.83

CX Basic pKa:

CX LogP: 2.69

CX LogD: 2.68

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.84

References

1. Lu Z, Ott GR, Anand R, Liu RQ, Covington MB, Vaddi K, Qian M, Newton RC, Christ DD, Trzaskos J, Duan JJ..  (2008)  Potent, selective, orally bioavailable inhibitors of tumor necrosis factor-alpha converting enzyme (TACE): discovery of indole, benzofuran, imidazopyridine and pyrazolopyridine P1' substituents.,  18  (6): [PMID:18282708] [10.1016/j.bmcl.2008.01.120]

2. Georgiadis D, Yiotakis A..  (2008)  Specific targeting of metzincin family members with small-molecule inhibitors: progress toward a multifarious challenge.,  16  (19): [PMID:18790648] [10.1016/j.bmc.2008.08.058]

Source

Source(1):

• Scientific Literature