2-(5'-Amidino-2,2'-bithiophen-5-yl)-1H-benzimidazole-5(6)-amidine

ID: ALA4169899

PubChem CID: 145955805

Max Phase: Preclinical

Molecular Formula: C17H14N6S2

Molecular Weight: 366.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2nc(-c3ccc(-c4ccc(C(=N)N)s4)s3)[nH]c2c1

Standard InChI:  InChI=1S/C17H14N6S2/c18-15(19)8-1-2-9-10(7-8)23-17(22-9)14-6-4-12(25-14)11-3-5-13(24-11)16(20)21/h1-7H,(H3,18,19)(H3,20,21)(H,22,23)

Standard InChI Key:  TZERAARLTVPLOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   27.9317   -2.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9305   -3.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6386   -3.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6368   -2.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3454   -2.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3457   -3.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1286   -3.4964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6123   -2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1282   -2.1645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4279   -2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9084   -3.4911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.6856   -3.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6853   -2.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9080   -2.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3466   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3469   -4.5323    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.1242   -4.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6043   -4.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1237   -3.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3770   -5.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8304   -6.1692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1764   -5.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2225   -3.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5151   -3.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2218   -4.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 10  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  2  0
 12 15  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
  2 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4169899

   ---

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: 366.48

Molecular Weight (Monoisotopic): 366.0721

AlogP: 3.59

#Rotatable Bonds: 4

Polar Surface Area: 128.42

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.81

CX Basic pKa: 11.39

CX LogP: 1.33

CX LogD: -1.22

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: -0.56

References

1. Farahat AA, Ismail MA, Kumar A, Wenzler T, Brun R, Paul A, Wilson WD, Boykin DW..  (2018)  Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity.,  143  [PMID:29126729] [10.1016/j.ejmech.2017.10.056]

Source

Source(1):

• Scientific Literature