5-(3-(benzyl(methyl)amino)-4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

ID: ALA2282811

PubChem CID: 49823547

Max Phase: Preclinical

Molecular Formula: C20H22ClN5

Molecular Weight: 367.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc(N)nc(N)c1-c1ccc(Cl)c(N(C)Cc2ccccc2)c1

Standard InChI:  InChI=1S/C20H22ClN5/c1-3-16-18(19(22)25-20(23)24-16)14-9-10-15(21)17(11-14)26(2)12-13-7-5-4-6-8-13/h4-11H,3,12H2,1-2H3,(H4,22,23,24,25)

Standard InChI Key:  KCDGAWMTJFRVMI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   18.6908   -3.4379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6897   -4.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3977   -4.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1074   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1045   -3.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3959   -3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8077   -3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5172   -3.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2229   -3.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2202   -2.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5060   -1.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8033   -2.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8157   -4.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8170   -5.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9816   -4.6655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3935   -2.2119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9259   -1.7912    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.9319   -3.4277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9346   -4.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6383   -3.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6437   -4.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6448   -5.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3530   -5.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0604   -5.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0550   -4.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3463   -4.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
  4 13  1  0
 13 14  1  0
  2 15  1  0
  6 16  1  0
 10 17  1  0
  9 18  1  0
 18 19  1  0
 18 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282811

   5-[3-[Benzyl(methyl)amino]-4-chlorophenyl]-6-ethylpyrimidine-2,4-diamine

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: 367.88

Molecular Weight (Monoisotopic): 367.1564

AlogP: 4.16

#Rotatable Bonds: 5

Polar Surface Area: 81.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.77

CX LogP: 4.58

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.15

References

1. Kiani YS, Kalsoom S, Riaz N.  (2013)  In silico ligand-based pharmacophore model generation for the identification of novel Pneumocystis carinii DHFR inhibitors,  22  (2): [10.1007/s00044-012-0082-2]

Source

Source(1):

• Scientific Literature