(3S,4S)-tert-butyl 3-(hydroxycarbamoyl)-4-(4-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzamido)pyrrolidine-1-carboxylate

ID: ALA403186

Chembl Id: CHEMBL403186

PubChem CID: 10163627

Max Phase: Preclinical

Molecular Formula: C26H31N5O5

Molecular Weight: 493.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccccc2n1Cc1ccc(C(=O)N[C@@H]2CN(C(=O)OC(C)(C)C)C[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C26H31N5O5/c1-16-27-20-7-5-6-8-22(20)31(16)13-17-9-11-18(12-10-17)23(32)28-21-15-30(14-19(21)24(33)29-35)25(34)36-26(2,3)4/h5-12,19,21,35H,13-15H2,1-4H3,(H,28,32)(H,29,33)/t19-,21+/m0/s1

Standard InChI Key:  WMWPLQAXVKBJIC-PZJWPPBQSA-N

Alternative Forms

1. Parent:

   

   ALA403186

   tert-butyl (3S,4S)-3-(hydroxycarbamoyl)-4-({4-[(2-methyl-1H-1,3-benzodiazol-1-yl)methyl]benzene}amido)pyrrolidine-1-carboxylate

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

Calculated Properties

Molecular Weight: 493.56

Molecular Weight (Monoisotopic): 493.2325

AlogP: 2.86

#Rotatable Bonds: 5

Polar Surface Area: 125.79

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.84

CX Basic pKa: 5.86

CX LogP: 2.07

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: -1.19

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