2-(4'-Amidinobiphenyl-4-yl)-5-amidino-1H-indole dihydrochloride

ID: ALA3216972

PubChem CID: 90665084

Max Phase: Preclinical

Molecular Formula: C22H21Cl2N5

Molecular Weight: 353.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)c1ccc(-c2ccc(-c3cc4cc(C(=N)N)ccc4[nH]3)cc2)cc1

Standard InChI:  InChI=1S/C22H19N5.2ClH/c23-21(24)16-7-3-14(4-8-16)13-1-5-15(6-2-13)20-12-18-11-17(22(25)26)9-10-19(18)27-20;;/h1-12,27H,(H3,23,24)(H3,25,26);2*1H

Standard InChI Key:  LRCOVZLJQBPMGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   16.4078    0.5203    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896    0.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2418   -1.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791   -0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4199    1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    1.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5763   -0.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4157    0.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9120    0.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5690   -0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7297   -1.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2334   -1.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0659   -0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7391    0.3915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5900   -1.6814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251    2.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549    0.8867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9078    0.5203    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
  4  7  2  0
 14 15  1  0
  2  3  2  0
 15 16  2  0
 16 11  1  0
  6  5  2  0
 14 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
 10  6  1  0
 20 21  1  0
  5  2  1  0
 21 22  2  0
 22 17  1  0
  9 11  1  0
 20 23  1  0
  6  7  1  0
 23 24  1  0
 11 12  2  0
 23 25  2  0
  2 26  1  0
 12 13  1  0
 26 27  2  0
  3  4  1  0
 26 28  1  0
M  END

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: 353.43

Molecular Weight (Monoisotopic): 353.1640

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 115.53

Molecular Species: BASE

HBA: 2

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.66

CX LogP: 3.13

CX LogD: -1.68

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -0.37

References

1. Farahat AA, Kumar A, Say M, Barghash Ael-D, Goda FE, Eisa HM, Wenzler T, Brun R, Liu Y, Mickelson L, Wilson WD, Boykin DW..  (2010)  Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines.,  18  (2): [PMID:20031421] [10.1016/j.bmc.2009.12.011]

Source

Source(1):

• Scientific Literature