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

ID: ALA1278183

PubChem CID: 25330802

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)c1ccoc1

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

Standard InChI Key:  PESPKMJWELMGKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -4.2181   -4.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193   -5.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044   -5.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -3.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -4.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906   -5.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0001   -5.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -4.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006   -4.0810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6901   -4.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779   -5.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463   -5.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -4.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -4.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2807   -4.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519   -3.3195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769   -3.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866   -2.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1922   -4.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031   -2.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715   -1.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554   -1.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.8481    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  2  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1278183

   N-[3-(1H-benzimidazol-2-yl)phenyl]furan-3-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: 3.52

CX LogD: 3.51

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.38

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. 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(1):

• Scientific Literature