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

ID: ALA152975

PubChem CID: 15723792

Max Phase: Preclinical

Molecular Formula: C14H17N5O3

Molecular Weight: 303.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1nc2cc(C(=O)N3CCNCC3)ccc2[nH]1

Standard InChI:  InChI=1S/C14H17N5O3/c1-22-14(21)18-13-16-10-3-2-9(8-11(10)17-13)12(20)19-6-4-15-5-7-19/h2-3,8,15H,4-7H2,1H3,(H2,16,17,18,21)

Standard InChI Key:  HOWJUTDWQYZHEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  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
    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
    3.1750   -4.7792    0.0000 C   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
    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
    1.0292   -3.5417    0.0000 O   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
    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
   -0.3958   -4.3625    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   -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
    6.9125   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  8  1  0
  6  2  1  0
  7  5  1  0
  8 11  1  0
  9  4  1  0
 10  3  1  0
 11  6  2  0
 12  5  2  0
 13 20  1  0
 14  9  2  0
 15 16  1  0
 16 10  2  0
 17  9  1  0
 18  7  1  0
 19  7  1  0
 20 19  1  0
 21 18  1  0
 22 17  1  0
 10  6  1  0
 15  8  2  0
 13 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA152975

   methyl N-[6-(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: 303.32

Molecular Weight (Monoisotopic): 303.1331

AlogP: 0.79

#Rotatable Bonds: 2

Polar Surface Area: 99.35

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: 7.80

CX LogP: 0.36

CX LogD: 0.00

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -1.43

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