ID: ALA253275

Max Phase: Preclinical

Molecular Formula: C22H21F3N4O4

Molecular Weight: 462.43

Molecule Type: Small molecule

Representations

Synonyms (1): BMS-566394
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(N[C@@H]1CCOC[C@@H]1C(=O)NO)c1ccc(Cn2c(C(F)(F)F)nc3ccccc32)cc1

Standard InChI:  InChI=1S/C22H21F3N4O4/c23-22(24,25)21-27-17-3-1-2-4-18(17)29(21)11-13-5-7-14(8-6-13)19(30)26-16-9-10-33-12-15(16)20(31)28-32/h1-8,15-16,32H,9-12H2,(H,26,30)(H,28,31)/t15-,16+/m0/s1

Standard InChI Key:  PGVYYPZKXKGBLD-JKSUJKDBSA-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: 2.74

#Rotatable Bonds: 5

Polar Surface Area: 105.48

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: 2.43

CX LogP: 2.30

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -1.09

References

1. Ott GR, Asakawa N, Lu Z, Anand R, Liu RQ, Covington MB, Vaddi K, Qian M, Newton RC, Christ DD, Trzaskos JM, Duan JJ..  (2008)  Potent, exceptionally selective, orally bioavailable inhibitors of TNF-alpha Converting Enzyme (TACE): novel 2-substituted-1H-benzo[d]imidazol-1-yl)methyl)benzamide P1' substituents.,  18  (5): [PMID:18242982] [10.1016/j.bmcl.2008.01.075]

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]

3. Sengupta P, Puri CS, Chokshi HA, Sheth CK, Midha AS, Chitturi TR, Thennati R, Murumkar PR, Yadav MR..  (2011)  Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE.,  46  (11): [PMID:21963348] [10.1016/j.ejmech.2011.09.018]

Source

Source(1):

• Scientific Literature