5-(4-Chlorophenyl)-6-propylpyrimidine-2,4-diamine

ID: ALA3577317

PubChem CID: 23423607

Max Phase: Preclinical

Molecular Formula: C13H15ClN4

Molecular Weight: 262.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1nc(N)nc(N)c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C13H15ClN4/c1-2-3-10-11(12(15)18-13(16)17-10)8-4-6-9(14)7-5-8/h4-7H,2-3H2,1H3,(H4,15,16,17,18)

Standard InChI Key:  YEXIBPDKYUNGGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2955   -5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -6.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0067   -7.2009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9395   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  6  9  1  0
  1 15  1  0
 12 16  1  0
  7 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577317

   5-(4-Chlorophenyl)-6-propylpyrimidine-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: 262.74

Molecular Weight (Monoisotopic): 262.0985

AlogP: 2.91

#Rotatable Bonds: 3

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: 7.74

CX LogP: 3.19

CX LogD: 2.70

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.89

Np Likeness Score: -0.78

References

1. 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]

2. Guo, Peng P and 5 more authors.  2013-06-13  Development of Unsymmetrical Dyads As Potent Noncarbohydrate-Based Inhibitors against Human β-N-Acetyl-d-hexosaminidase.  [PMID:24900704]

3. Selnick, Harold G and 21 more authors.  2019-11-27  Discovery of MK-8719, a Potent O-GlcNAcase Inhibitor as a Potential Treatment for Tauopathies.  [PMID:31487175]

Source

Source(1):

• Scientific Literature