N-(3-(1H-benzo[d]imidazol-2-yl)phenyl)furan-2-carboxamide

ID: ALA1278182

PubChem CID: 655022

Max Phase: Preclinical

Molecular Formula: C18H13N3O2

Molecular Weight: 303.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(-c2nc3ccccc3[nH]2)c1)c1ccco1

Standard InChI:  InChI=1S/C18H13N3O2/c22-18(16-9-4-10-23-16)19-13-6-3-5-12(11-13)17-20-14-7-1-2-8-15(14)21-17/h1-11H,(H,19,22)(H,20,21)

Standard InChI Key:  LWMXSFDBHXPLLD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   20.5319    0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5307   -0.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2456   -0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2438    1.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9591    0.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9594   -0.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7499   -0.3090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2382    0.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7494    1.0357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0599    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4721   -0.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2963   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7094    0.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2922    1.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4693    1.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7019    1.7971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5269    1.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9366    2.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9422    1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7536    2.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9220    3.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2059    3.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5950    3.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  5  4  2  0
 14 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 17 19  2  0
 18 20  1  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1278182

   N-[3-(1H-benzimidazol-2-yl)phenyl]furan-2-carboxamide

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): 303.1008

AlogP: 4.08

#Rotatable Bonds: 3

Polar Surface Area: 70.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: 5.12

CX LogP: 3.44

CX LogD: 3.43

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.86

References

1. Keurulainen L, Salin O, Siiskonen A, Kern JM, Alvesalo J, Kiuru P, Maass M, Yli-Kauhaluoma J, Vuorela P..  (2010)  Design and synthesis of 2-arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae.,  53  (21): [PMID:20932010] [10.1021/jm1008083]

2. PubChem BioAssay data set, 

3. Keurulainen L, Siiskonen A, Nasereddin A, Kopelyanskiy D, Sacerdoti-Sierra N, Leino TO, Tammela P, Yli-Kauhaluoma J, Jaffe CL, Kiuru P..  (2015)  Synthesis and biological evaluation of 2-arylbenzimidazoles targeting Leishmania donovani.,  25  (9): [PMID:25827525] [10.1016/j.bmcl.2015.03.027]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays