5-((2-(7-chloroquinolin-4-ylamino)ethylamino)methyl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one

ID: ALA531738

PubChem CID: 6501965

Max Phase: Preclinical

Molecular Formula: C21H22ClN5O

Molecular Weight: 395.89

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(2): TCMDC-125236 | MMV665875

Canonical SMILES:  Cn1c(=O)n(C)c2cc(CNCCNc3ccnc4cc(Cl)ccc34)ccc21

Standard InChI:  InChI=1S/C21H22ClN5O/c1-26-19-6-3-14(11-20(19)27(2)21(26)28)13-23-9-10-25-17-7-8-24-18-12-15(22)4-5-16(17)18/h3-8,11-12,23H,9-10,13H2,1-2H3,(H,24,25)

Standard InChI Key:  NPWXHTXMBIOHKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.9553  -10.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316  -10.5455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6858   -9.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982   -8.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -8.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4344   -8.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3032   -8.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3088   -7.3978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1776   -6.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1831   -5.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0519   -5.4075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575   -4.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9341   -3.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9384   -2.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0661   -2.3897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1950   -2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243   -2.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536   -2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861   -2.3959    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4536   -3.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243   -4.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1907   -3.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317   -9.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5537  -10.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3357  -11.3721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985  -12.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334  -11.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8261  -12.3308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 27  1  0
  2  3  1  0
  3 24  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 22  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 22  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  6 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA531738

   5-[[2-[(7-Chloroquinolin-4-yl)amino]ethylamino]methyl]-1,3-dimethylbenzimidazol-2-one

2. Alternative Forms:

   

   ALA531738

   5-[[2-[(7-Chloroquinolin-4-yl)amino]ethylamino]methyl]-1,3-dimethylbenzimidazol-2-one;hydrochloride

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: 395.89

Molecular Weight (Monoisotopic): 395.1513

AlogP: 3.28

#Rotatable Bonds: 6

Polar Surface Area: 63.88

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 2.83

CX LogD: 1.24

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.45

References

1. Pereira GAN,da Silva EB,Braga SFP,Leite PG,Martins LC,Vieira RP,Soh WT,Villela FS,Costa FMR,Ray D,de Andrade SF,Brandstetter H,Oliveira RB,Caffrey CR,Machado FS,Ferreira RS.  (2019)  Discovery and characterization of trypanocidal cysteine protease inhibitors from the 'malaria box'.,  179  [PMID:31284086] [10.1016/j.ejmech.2019.06.062]

Source

Source(1):

• Scientific Literature