[5-(4-Dimethylcarbamoyl-piperazine-1-carbonyl)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester

ID: ALA151025

PubChem CID: 15723793

Max Phase: Preclinical

Molecular Formula: C17H22N6O4

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1nc2cc(C(=O)N3CCN(C(=O)N(C)C)CC3)ccc2[nH]1

Standard InChI:  InChI=1S/C17H22N6O4/c1-21(2)17(26)23-8-6-22(7-9-23)14(24)11-4-5-12-13(10-11)19-15(18-12)20-16(25)27-3/h4-5,10H,6-9H2,1-3H3,(H2,18,19,20,25)

Standard InChI Key:  ZWSBRKFQOCZSRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.4500   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -4.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -5.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -5.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -5.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -4.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -5.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -6.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -6.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -3.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  7  1  0
  4  1  1  0
  5  1  1  0
  6 10  1  0
  7 17  1  0
  8  6  1  0
  9  2  1  0
 10 13  1  0
 11  5  1  0
 12  4  1  0
 13  9  2  0
 14  3  1  0
 15  3  2  0
 16 18  1  0
 17 19  1  0
 18  8  1  0
 19  8  1  0
 20  6  2  0
 21 11  2  0
 22 23  1  0
 23 12  2  0
 24 11  1  0
 25 14  1  0
 26 14  1  0
 27 24  1  0
 12  9  1  0
 22 10  2  0
  7 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA151025

   methyl N-[6-[4-(dimethylcarbamoyl)piperazine-1-carbonyl]-1H-benzimidazol-2-yl]carbamate

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: 374.40

Molecular Weight (Monoisotopic): 374.1703

AlogP: 1.18

#Rotatable Bonds: 2

Polar Surface Area: 110.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: 3.46

CX LogP: 0.29

CX LogD: 0.28

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -1.56

References

1. Ram S, Wise DS, Wotring LL, McCall JW, Townsend LB..  (1992)  Synthesis and biological activity of certain alkyl 5-(alkoxycarbonyl)-1H-benzimidazole-2-carbamates and related derivatives: a new class of potential antineoplastic and antifilarial agents.,  35  (3): [PMID:1738146] [10.1021/jm00081a016]

Source

Source(1):

• Scientific Literature