ID: ALA447787

Max Phase: Preclinical

Molecular Formula: C28H35N5O5

Molecular Weight: 521.62

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)c1nc2ccccc2n1Cc1ccc(C(=O)N[C@@H]2CN(C(=O)OC(C)(C)C)C[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C28H35N5O5/c1-17(2)24-29-21-8-6-7-9-23(21)33(24)14-18-10-12-19(13-11-18)25(34)30-22-16-32(15-20(22)26(35)31-37)27(36)38-28(3,4)5/h6-13,17,20,22,37H,14-16H2,1-5H3,(H,30,34)(H,31,35)/t20-,22+/m0/s1

Standard InChI Key:  HWRTYSUSQVJAGF-RBBKRZOGSA-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: 521.62

Molecular Weight (Monoisotopic): 521.2638

AlogP: 3.68

#Rotatable Bonds: 6

Polar Surface Area: 125.79

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.84

CX Basic pKa: 5.62

CX LogP: 3.31

CX LogD: 3.29

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.34

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]

Source

Source(1):

• Scientific Literature