2-(4-((1H-benzo[d]imidazol-2-yl)methyl)-1,4-diazepan-1-yl)-N-(4-chlorophenyl)acetamide

ID: ALA1097550

PubChem CID: 46888272

Max Phase: Preclinical

Molecular Formula: C21H24ClN5O

Molecular Weight: 397.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1CCCN(Cc2nc3ccccc3[nH]2)CC1)Nc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H24ClN5O/c22-16-6-8-17(9-7-16)23-21(28)15-27-11-3-10-26(12-13-27)14-20-24-18-4-1-2-5-19(18)25-20/h1-2,4-9H,3,10-15H2,(H,23,28)(H,24,25)

Standard InChI Key:  YPHVDEBUZZGZRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -5.4048  -14.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4002  -14.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837  -15.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6982  -13.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807  -14.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704  -14.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089  -14.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1913  -13.7596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690  -14.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072  -15.1088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800  -14.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022  -15.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201  -15.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0480  -16.3815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205  -16.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328  -16.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674  -16.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821  -16.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821  -15.5576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111  -16.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5279  -16.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341  -16.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341  -15.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5204  -15.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8094  -15.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524  -15.1527    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820  -15.0964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966  -16.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  7  8  2  0
  8  5  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 12 14  1  0
 13 15  1  0
 14 16  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
  1  2  2  0
  6 27  1  0
 27  7  1  0
 18 28  1  0
 28 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097550

   2-[4-(1H-benzimidazol-2-ylmethyl)-1,4-diazepan-1-yl]-N-(4-chlorophenyl)acetamide

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: 397.91

Molecular Weight (Monoisotopic): 397.1669

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 64.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.48

CX Basic pKa: 6.75

CX LogP: 2.70

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -2.25

References

1. Gu SJ, Lee JK, Pae AN, Chung HJ, Rhim H, Han SY, Min SJ, Cho YS..  (2010)  Synthesis and biological evaluation of 1,4-diazepane derivatives as T-type calcium channel blockers.,  20  (9): [PMID:20382529] [10.1016/j.bmcl.2010.03.084]

Source

Source(1):

• Scientific Literature