2-[(4-Amidino-3-fluorophenyl)ethynyl]-6-amidino-1Hindole dihydrochloride

ID: ALA3217179

PubChem CID: 90665199

Max Phase: Preclinical

Molecular Formula: C18H16Cl2FN5

Molecular Weight: 319.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)c1ccc2cc(C#Cc3ccc(C(=N)N)c(F)c3)[nH]c2c1

Standard InChI:  InChI=1S/C18H14FN5.2ClH/c19-15-7-10(2-6-14(15)18(22)23)1-5-13-8-11-3-4-12(17(20)21)9-16(11)24-13;;/h2-4,6-9,24H,(H3,20,21)(H3,22,23);2*1H

Standard InChI Key:  LFYHRMCNDDBHCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   14.8565   -0.7370    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
   -3.6217   -1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560   -0.8780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -2.6865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    0.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0887    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8534   -1.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3533   -1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0885    0.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3237    1.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    1.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5892    0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2028   -0.9076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1758    1.1705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9651   -2.2364    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.3565   -0.7370    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
  3  4  1  0
  9 14  1  0
  4  7  2  0
 14 15  3  0
  2  3  2  0
 15 16  1  0
  6  5  2  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9 10  2  0
 19 20  1  0
 10  6  1  0
 20 21  2  0
 21 16  1  0
  5  2  1  0
 19 22  1  0
  3 11  1  0
 22 23  1  0
  6  7  1  0
 22 24  2  0
 11 12  2  0
 18 25  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: 319.34

Molecular Weight (Monoisotopic): 319.1233

AlogP: 2.27

#Rotatable Bonds: 2

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: 13.74

CX Basic pKa: 11.18

CX LogP: 2.10

CX LogD: -2.29

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.28

Np Likeness Score: -0.71

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