2-(5-(5-Amidinothiophen-2-yl)furan-2-yl)-1H-indole-6-amidine

ID: ALA4175994

PubChem CID: 145973597

Max Phase: Preclinical

Molecular Formula: C18H15N5OS

Molecular Weight: 349.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2cc(-c3ccc(-c4ccc(C(=N)N)s4)o3)[nH]c2c1

Standard InChI:  InChI=1S/C18H15N5OS/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:  IDZZPBSNWWHZPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.6842   -7.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831   -8.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911   -8.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -7.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979   -7.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982   -8.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8812   -8.8412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3649   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8807   -7.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1804   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6610   -8.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4381   -8.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4378   -7.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6605   -7.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0991   -9.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0994   -9.8771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8767  -10.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3569   -9.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8762   -8.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1295  -10.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5829  -11.5139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9289  -11.0761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -8.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676   -8.5858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -9.8122    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:

   

   ALA4175994

   ---

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: 349.42

Molecular Weight (Monoisotopic): 349.0997

AlogP: 3.72

#Rotatable Bonds: 4

Polar Surface Area: 128.67

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.04

CX Basic pKa: 11.15

CX LogP: 1.93

CX LogD: -1.48

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: -0.47

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