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

ID: ALA1278093

PubChem CID: 25506900

Max Phase: Preclinical

Molecular Formula: C18H13N3OS

Molecular Weight: 319.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(-c2nc3ccccc3[nH]2)c1)c1ccsc1

Standard InChI:  InChI=1S/C18H13N3OS/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:  WKVRQTGROORAEO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.8077    1.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8065    0.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2351    1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354    0.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0261   -0.0006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5144    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256    1.3442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3363    0.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7485   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5729   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9860    0.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5688    1.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7457    1.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9785    2.1059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8037    2.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2134    2.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2190    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0306    2.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1990    3.7177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4829    4.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8718    3.5730    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:

   

   ALA1278093

   N-[3-(1H-benzimidazol-2-yl)phenyl]thiophene-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: 319.39

Molecular Weight (Monoisotopic): 319.0779

AlogP: 4.54

#Rotatable Bonds: 3

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: 4.16

CX LogD: 4.15

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -2.29

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