N-(3-(1H-benzo[d]imidazol-2-yl)phenyl)-2-(thiophen-2-yl)acetamide

ID: ALA1278181

PubChem CID: 889712

Max Phase: Preclinical

Molecular Formula: C19H15N3OS

Molecular Weight: 333.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccs1)Nc1cccc(-c2nc3ccccc3[nH]2)c1

Standard InChI:  InChI=1S/C19H15N3OS/c23-18(12-15-7-4-10-24-15)20-14-6-3-5-13(11-14)19-21-16-8-1-2-9-17(16)22-19/h1-11H,12H2,(H,20,23)(H,21,22)

Standard InChI Key:  AVQPSMBUPKXNHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   11.9902    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9891   -0.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7039   -0.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7021    1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4175    0.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4177   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2082   -0.4090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6965    0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2078    0.9357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5183    0.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9304   -0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7546   -0.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1677    0.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7505    0.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9277    0.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1602    1.6971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9852    1.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3950    2.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4005    0.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2200    2.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7027    1.7551    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.4863    2.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4831    2.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6975    3.0899    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
  9  5  1  0
 18 20  1  0
 20 21  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1278181

   N-[3-(1H-Benzoimidazol-2-yl)-phenyl]-2-thiophen-2-yl-acetamide

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: 333.42

Molecular Weight (Monoisotopic): 333.0936

AlogP: 4.47

#Rotatable Bonds: 4

Polar Surface Area: 57.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: 5.12

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -2.24

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