6-Ethyl-5-(4-methoxy-phenyl)-pyrimidine-2,4-diamine

ID: ALA281412

Cas Number: 113512-19-9

PubChem CID: 13926986

Max Phase: Preclinical

Molecular Formula: C13H16N4O

Molecular Weight: 244.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H16N4O/c1-3-10-11(12(14)17-13(15)16-10)8-4-6-9(18-2)7-5-8/h4-7H,3H2,1-2H3,(H4,14,15,16,17)

Standard InChI Key:  SRYOSRABCMAHOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  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
    1.0667   -1.6792    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
    0.0917   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -0.7667    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 13  1  0
 13 11  2  0
 14 10  1  0
 15  5  1  0
 16 12  1  0
 17 16  1  0
 18 15  1  0
  5  3  2  0
 14 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA281412

   6-Ethyl-5-(4-methoxyphenyl)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: 244.30

Molecular Weight (Monoisotopic): 244.1324

AlogP: 1.88

#Rotatable Bonds: 3

Polar Surface Area: 87.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.78

CX LogP: 1.99

CX LogD: 1.47

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -0.58

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. 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]

3. 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