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

ID: ALA4162632

PubChem CID: 145957511

Max Phase: Preclinical

Molecular Formula: C18H15N5S2

Molecular Weight: 365.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2cc(-c3ccc(-c4ccc(C(=N)N)s4)s3)[nH]c2c1

Standard InChI:  InChI=1S/C18H15N5S2/c19-17(20)10-2-1-9-7-12(23-11(9)8-10)13-3-4-14(24-13)15-5-6-16(25-15)18(21)22/h1-8,23H,(H3,19,20)(H3,21,22)

Standard InChI Key:  JLDNVNXUYNUWTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   15.8265   -2.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8254   -3.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5334   -3.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5316   -2.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2402   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2405   -3.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0235   -3.7069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5072   -3.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0231   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3227   -3.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8033   -3.7016    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5804   -3.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5801   -2.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8028   -2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2414   -3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2417   -4.7428    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.0190   -4.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4992   -4.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0185   -3.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2718   -5.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7252   -6.3796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0712   -5.9418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1173   -3.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4099   -3.4516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1167   -4.6779    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:

   

   ALA4162632

   ---

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: 365.49

Molecular Weight (Monoisotopic): 365.0769

AlogP: 4.19

#Rotatable Bonds: 4

Polar Surface Area: 115.53

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.74

CX Basic pKa: 11.16

CX LogP: 2.81

CX LogD: -0.90

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: -0.33

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