[5-(4-Fluoro-benzoylamino)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester

ID: ALA346208

PubChem CID: 15723797

Max Phase: Preclinical

Molecular Formula: C16H13FN4O3

Molecular Weight: 328.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1nc2cc(NC(=O)c3ccc(F)cc3)ccc2[nH]1

Standard InChI:  InChI=1S/C16H13FN4O3/c1-24-16(23)21-15-19-12-7-6-11(8-13(12)20-15)18-14(22)9-2-4-10(17)5-3-9/h2-8H,1H3,(H,18,22)(H2,19,20,21,23)

Standard InChI Key:  FTFRARZHXYKTHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  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
    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 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
    1.0292   -4.3667    0.0000 N   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
   -0.3958   -4.3667    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
    0.3167   -5.6042    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
    2.4542   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -4.7792    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
    1.7417   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375   -3.1292    0.0000 F   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  2  1  0
  6  9  1  0
  7  4  1  0
  8  3  1  0
  9 12  1  0
 10  5  2  0
 11  6  1  0
 12 10  1  0
 13  6  2  0
 14  7  2  0
 15  8  2  0
 16 11  2  0
 17 11  1  0
 18  7  1  0
 19 15  1  0
 20 21  1  0
 21 17  2  0
 22 16  1  0
 23 20  1  0
 24 18  1  0
  8  5  1  0
 19 12  2  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA346208

   methyl N-[6-[(4-fluorobenzoyl)amino]-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: 328.30

Molecular Weight (Monoisotopic): 328.0972

AlogP: 3.13

#Rotatable Bonds: 3

Polar Surface Area: 96.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.72

CX Basic pKa: 4.26

CX LogP: 3.04

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -1.67

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