1-[5-(4-Bromo-2-chlorophenyl)-2-furyl]-N-(4-piperidinylmethyl)methanamine dihydrochloride

ID: ALA4793916

PubChem CID: 17151695

Max Phase: Preclinical

Molecular Formula: C17H22BrCl3N2O

Molecular Weight: 383.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Cl.Clc1cc(Br)ccc1-c1ccc(CNCC2CCNCC2)o1

Standard InChI:  InChI=1S/C17H20BrClN2O.2ClH/c18-13-1-3-15(16(19)9-13)17-4-2-14(22-17)11-21-10-12-5-7-20-8-6-12;;/h1-4,9,12,20-21H,5-8,10-11H2;2*1H

Standard InChI Key:  PKHDVCAJNNWLPS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   38.6763   -2.5671    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.6855   -3.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8660   -3.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4555   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8594   -4.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6820   -4.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0929   -4.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6350   -4.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1540   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3714   -3.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3670   -4.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1470   -4.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6993   -4.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9504   -4.6399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.2826   -5.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5378   -4.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8701   -5.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4525   -3.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7077   -3.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0400   -4.1038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1212   -4.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9143   -4.1006    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   43.4616   -2.6717    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.0477   -6.5251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  4  8  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 17 21  1  0
 19 20  1  0
 20 21  1  0
  7 22  1  0
  3 23  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.72

Molecular Weight (Monoisotopic): 382.0448

AlogP: 4.45

#Rotatable Bonds: 5

Polar Surface Area: 37.20

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.38

CX LogP: 3.64

CX LogD: -0.86

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: -1.05

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