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

ID: ALA4173700

PubChem CID: 145950596

Max Phase: Preclinical

Molecular Formula: C18H15N5O2

Molecular Weight: 333.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2cc(-c3ccc(-c4ccc(C(=N)N)o4)o3)[nH]c2c1

Standard InChI:  InChI=1S/C18H15N5O2/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:  CGQTZYDECVIQSQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.5893   -1.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5881   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2962   -3.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0033   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7862   -2.9640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2699   -2.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7858   -1.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0855   -2.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5661   -2.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3432   -2.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3429   -1.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5656   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0042   -3.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045   -3.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7818   -4.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2619   -3.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7813   -2.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0346   -5.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4880   -5.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8340   -5.1989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -2.7086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -3.9350    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:

   

   ALA4173700

   ---

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: 333.35

Molecular Weight (Monoisotopic): 333.1226

AlogP: 3.26

#Rotatable Bonds: 4

Polar Surface Area: 141.81

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.01

CX Basic pKa: 11.15

CX LogP: 0.99

CX LogD: -1.45

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.29

Np Likeness Score: -0.42

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