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

ID: ALA1098508

PubChem CID: 46888334

Max Phase: Preclinical

Molecular Formula: C22H27N5O2

Molecular Weight: 393.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)CN2CCCN(Cc3nc4ccccc4[nH]3)CC2)cc1

Standard InChI:  InChI=1S/C22H27N5O2/c1-29-18-9-7-17(8-10-18)23-22(28)16-27-12-4-11-26(13-14-27)15-21-24-19-5-2-3-6-20(19)25-21/h2-3,5-10H,4,11-16H2,1H3,(H,23,28)(H,24,25)

Standard InChI Key:  BEXYYUBKFYUJAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -3.4480    1.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324   -0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7406    1.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0147    0.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392    0.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2309    1.4646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473    0.1282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562   -0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -1.1451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -1.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191   -1.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3361   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3361   -0.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -1.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798   -1.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1885   -1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1885   -0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    0.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7645   -0.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9065    0.0794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6227   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276    0.1306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522   -1.5583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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
 26 27  1  0
  2  3  1  0
  3  6  2  0
  6 28  1  0
 28  7  1  0
 18 29  1  0
 29 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098508

   2-[4-(1H-benzimidazol-2-ylmethyl)-1,4-diazepan-1-yl]-N-(4-methoxyphenyl)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: 393.49

Molecular Weight (Monoisotopic): 393.2165

AlogP: 2.72

#Rotatable Bonds: 6

Polar Surface Area: 73.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.48

CX Basic pKa: 6.78

CX LogP: 1.94

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.99

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