N-(3,4-dichlorobenzyl)-4-(3,4-dimethoxyphenyl)pyrimidin-2-amine

ID: ALA2392366

PubChem CID: 46926509

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N3O2

Molecular Weight: 390.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccnc(NCc3ccc(Cl)c(Cl)c3)n2)cc1OC

Standard InChI:  InChI=1S/C19H17Cl2N3O2/c1-25-17-6-4-13(10-18(17)26-2)16-7-8-22-19(24-16)23-11-12-3-5-14(20)15(21)9-12/h3-10H,11H2,1-2H3,(H,22,23,24)

Standard InChI Key:  VGQKWMLIBUTHGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   23.7549  -28.6429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7538  -29.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4618  -29.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1715  -29.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1686  -28.6393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4600  -28.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8763  -29.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8763  -30.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5838  -31.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5798  -29.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4576  -27.4169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1641  -27.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8730  -27.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8733  -28.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5814  -28.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2888  -28.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2837  -27.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5751  -26.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2848  -29.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2949  -30.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0074  -31.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7144  -30.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7043  -29.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9872  -29.4385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9888  -26.9882    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.9983  -28.6284    0.0000 Cl  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 20  2  0
 19 10  2  0
 10  7  1  0
  4  7  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 23 24  1  0
 17 25  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2392366

   N-[(3,4-dichlorophenyl)methyl]-4-(3,4-dimethoxyphenyl)pyrimidin-2-amine

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: 390.27

Molecular Weight (Monoisotopic): 389.0698

AlogP: 5.08

#Rotatable Bonds: 6

Polar Surface Area: 56.27

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.92

CX LogP: 4.85

CX LogD: 4.85

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: -1.18

References

1. Coombs TC, Tanega C, Shen M, Wang JL, Auld DS, Gerritz SW, Schoenen FJ, Thomas CJ, Aubé J..  (2013)  Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: development of chemical probe ML315.,  23  (12): [PMID:23642479] [10.1016/j.bmcl.2013.02.096]

Source

Source(1):

• Scientific Literature