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

ID: ALA4173328

PubChem CID: 136072243

Max Phase: Preclinical

Molecular Formula: C17H14N6O2

Molecular Weight: 334.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2nc(-c3ccc(-c4ccc(C(=N)N)o4)o3)[nH]c2c1

Standard InChI:  InChI=1S/C17H14N6O2/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:  ZYSPYCCIMQTPAU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   15.5624   -9.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5612  -10.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2693  -10.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2675   -8.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9761   -9.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9763  -10.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7593  -10.4590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2430   -9.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7589   -9.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0586   -9.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5391  -10.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3163  -10.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3160   -9.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5387   -9.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9773  -10.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9776  -11.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7549  -11.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2350  -11.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7544  -10.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0077  -12.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4611  -13.1318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8071  -12.6939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8532  -10.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1458  -10.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8525  -11.4300    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:

   

   ALA4173328

   ---

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: 334.34

Molecular Weight (Monoisotopic): 334.1178

AlogP: 2.65

#Rotatable Bonds: 4

Polar Surface Area: 154.70

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.16

CX Basic pKa: 11.37

CX LogP: -1.02

CX LogD: -1.80

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.29

Np Likeness Score: -0.67

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