6-Ethyl-5-p-tolyl-pyrimidine-2,4-diamine

ID: ALA21778

PubChem CID: 11020649

Max Phase: Preclinical

Molecular Formula: C13H16N4

Molecular Weight: 228.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc(N)nc(N)c1-c1ccc(C)cc1

Standard InChI:  InChI=1S/C13H16N4/c1-3-10-11(12(14)17-13(15)16-10)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3,(H4,14,15,16,17)

Standard InChI Key:  BGGIEUCLTOKUIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -1.4833   -2.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -3.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -1.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750   -3.5625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  6  1  0
  6  4  2  0
  7  3  1  0
  8  2  1  0
  9  4  1  0
 10  7  2  0
 11  7  1  0
 12 11  2  0
 13 10  1  0
 14 12  1  0
 15  5  1  0
 16 14  1  0
 17 15  1  0
  5  3  2  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA21778

   6-Ethyl-5-(4-methylphenyl)pyrimidine-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: 228.30

Molecular Weight (Monoisotopic): 228.1375

AlogP: 2.18

#Rotatable Bonds: 2

Polar Surface Area: 77.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.78

CX LogP: 2.66

CX LogD: 2.14

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.83

Np Likeness Score: -0.76

References

1. Tarnchompoo B, Sirichaiwat C, Phupong W, Intaraudom C, Sirawaraporn W, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y..  (2002)  Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.,  45  (6): [PMID:11881993] [10.1021/jm010131q]

2. Kamchonwongpaisan S, Quarrell R, Charoensetakul N, Ponsinet R, Vilaivan T, Vanichtanankul J, Tarnchompoo B, Sirawaraporn W, Lowe G, Yuthavong Y..  (2004)  Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.,  47  (3): [PMID:14736247] [10.1021/jm030165t]

3. Parenti MD, Pacchioni S, Ferrari AM, Rastelli G..  (2004)  Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach.,  47  (17): [PMID:15293997] [10.1021/jm040769c]

4. Tropak MB, Zhang J, Yonekawa S, Rigat BA, Aulakh VS, Smith MR, Hwang HJ, Ciufolini MA, Mahuran DJ..  (2015)  Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β-N-acetylhexosaminidase Activity.,  58  (11): [PMID:25984755] [10.1021/jm5017895]

Source

Source(1):

• Scientific Literature