2-chloro-N-(2-{4-[(2-methylbenzene)amido]phenyl}-1H-1,3-benzodiazol-5-yl)benzamide

ID: ALA213665

PubChem CID: 44416625

Max Phase: Preclinical

Molecular Formula: C28H21ClN4O2

Molecular Weight: 480.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C(=O)Nc1ccc(-c2nc3cc(NC(=O)c4ccccc4Cl)ccc3[nH]2)cc1

Standard InChI:  InChI=1S/C28H21ClN4O2/c1-17-6-2-3-7-21(17)27(34)30-19-12-10-18(11-13-19)26-32-24-15-14-20(16-25(24)33-26)31-28(35)22-8-4-5-9-23(22)29/h2-16H,1H3,(H,30,34)(H,31,35)(H,32,33)

Standard InChI Key:  OQNXRKFQEIPFTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   14.1433  -13.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5442  -14.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3684  -14.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7916  -13.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3847  -12.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5619  -12.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3184  -13.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486  -11.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474  -12.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7622  -13.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4787  -12.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4758  -11.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7604  -11.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1938  -13.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1951  -14.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9076  -12.7746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6227  -13.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6193  -14.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3336  -14.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3296  -12.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8285  -12.9174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0445  -13.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0510  -14.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8400  -14.2525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7620  -14.0152    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6165  -13.6219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0200  -14.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8449  -14.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5985  -15.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2463  -15.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0705  -15.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4928  -14.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0849  -13.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2621  -13.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8558  -12.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 17 18  2  0
  4  5  2  0
 18 19  1  0
 19 23  2  0
  9 10  1  0
 22 20  2  0
 20 17  1  0
 22 23  1  0
  2  3  2  0
 10 11  2  0
  5  6  1  0
 11 12  1  0
 21 22  1  0
 23 24  1  0
 24  7  1  0
  7 21  2  0
  6  1  2  0
 10 25  1  0
 12 13  2  0
  4 26  1  0
 13  8  1  0
 26 27  1  0
  1  2  1  0
 27 28  1  0
 11 14  1  0
 27 29  2  0
  1  7  1  0
 28 30  2  0
 14 15  2  0
 30 31  1  0
  3  4  1  0
 31 32  2  0
 14 16  1  0
 32 33  1  0
 33 34  2  0
 34 28  1  0
 16 17  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA213665

   N-[4-[6-[(2-chlorobenzoyl)amino]-1H-benzimidazol-2-yl]phenyl]-2-methylbenzamide

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: 480.96

Molecular Weight (Monoisotopic): 480.1353

AlogP: 6.70

#Rotatable Bonds: 5

Polar Surface Area: 86.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.54

CX Basic pKa: 5.14

CX LogP: 6.59

CX LogD: 6.58

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: -1.52

References

1. Wolkenberg SE, Zhao Z, Kapitskaya M, Webber AL, Petrukhin K, Tang YS, Dean DC, Hartman GD, Lindsley CW..  (2006)  Identification of potent agonists of photoreceptor-specific nuclear receptor (NR2E3) and preparation of a radioligand.,  16  (19): [PMID:16879962] [10.1016/j.bmcl.2006.07.056]

Source

Source(1):

• Scientific Literature