2-(benzo[d][1,3]dioxol-5-yl)-N-(4-methoxybenzyl)pyrimidin-4-amine

ID: ALA2392390

PubChem CID: 44820589

Max Phase: Preclinical

Molecular Formula: C19H17N3O3

Molecular Weight: 335.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2ccnc(-c3ccc4c(c3)OCO4)n2)cc1

Standard InChI:  InChI=1S/C19H17N3O3/c1-23-15-5-2-13(3-6-15)11-21-18-8-9-20-19(22-18)14-4-7-16-17(10-14)25-12-24-16/h2-10H,11-12H2,1H3,(H,20,21,22)

Standard InChI Key:  VRHLLEYTPDHVSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    0.8158   -2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8146   -3.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227   -4.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -2.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110   -1.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -2.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1109   -2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081   -1.6679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -1.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -0.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -0.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244   -0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -1.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176   -1.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.6821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1328   -2.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -2.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343   -3.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -3.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980   -3.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -2.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 22  2  0
 21  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
  8  1  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
 16 19  1  0
 19 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2392390

   2-(1,3-benzodioxol-5-yl)-N-[(4-methoxyphenyl)methyl]pyrimidin-4-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: 335.36

Molecular Weight (Monoisotopic): 335.1270

AlogP: 3.49

#Rotatable Bonds: 5

Polar Surface Area: 65.50

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.56

CX LogP: 3.80

CX LogD: 3.79

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -1.01

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