2-(4-carbamimidoyl-2-methylphenyl)-1H-indole-5-carboximidamide

ID: ALA1650578

PubChem CID: 53320554

Max Phase: Preclinical

Molecular Formula: C17H17N5

Molecular Weight: 291.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DB1192 | CHEMBL1650578|DB1192

Canonical SMILES:  Cc1cc(C(=N)N)ccc1-c1cc2cc(C(=N)N)ccc2[nH]1

Standard InChI:  InChI=1S/C17H17N5/c1-9-6-10(16(18)19)2-4-13(9)15-8-12-7-11(17(20)21)3-5-14(12)22-15/h2-8,22H,1H3,(H3,18,19)(H3,20,21)

Standard InChI Key:  WMNOADXUDNUMIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.8785   -7.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8785   -7.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5922   -8.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5922   -6.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3103   -7.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3150   -7.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1054   -8.1133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5893   -7.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0980   -6.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4165   -7.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8313   -8.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6517   -8.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0636   -7.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6489   -6.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8223   -6.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8876   -7.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3009   -8.1405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2984   -6.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1639   -6.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1620   -5.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513   -7.0351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4070   -6.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
 10 15  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 10  1  0
  3  6  1  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 16 18  2  0
  8  9  2  0
  1 19  1  0
  9  5  1  0
 19 20  2  0
 10 11  2  0
 19 21  1  0
  5  4  1  0
 15 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650578

   2-(4-carbamimidoyl-2-methylphenyl)-1H-indole-5-carboximidamide

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: 291.36

Molecular Weight (Monoisotopic): 291.1484

AlogP: 2.71

#Rotatable Bonds: 3

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: 11.73

CX LogP: 1.99

CX LogD: -2.81

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -0.43

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R..  (2009)  In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.,  53  (12): [PMID:19786604] [10.1128/aac.00422-09]

2. Farahat AA, Kumar A, Say M, Wenzler T, Brun R, Paul A, Wilson WD, Boykin DW..  (2017)  Exploration of DAPI analogues: Synthesis, antitrypanosomal activity, DNA binding and fluorescence properties.,  128  [PMID:28152428] [10.1016/j.ejmech.2017.01.037]

Source

Source(1):

• Scientific Literature