(R)-2-(1-Hydroxy-but-2-ylamino)-6-[3-(2-pyrimidinyl)phenylamino]-9-iso-propylpurine

ID: ALA2295960

PubChem CID: 76309393

Max Phase: Preclinical

Molecular Formula: C22H26N8O

Molecular Weight: 418.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H](O)Nc1nc(Nc2cccc(-c3ncccn3)c2)c2ncn(C(C)C)c2n1

Standard InChI:  InChI=1S/C22H26N8O/c1-4-7-17(31)27-22-28-20(18-21(29-22)30(13-25-18)14(2)3)26-16-9-5-8-15(12-16)19-23-10-6-11-24-19/h5-6,8-14,17,31H,4,7H2,1-3H3,(H2,26,27,28,29)/t17-/m1/s1

Standard InChI Key:  HQRGSBHKKKWODU-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    3.9220  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3117  -11.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9357  -15.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326  -14.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0212  -12.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5931  -10.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3838  -16.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1620  -13.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4380  -12.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1888  -14.8179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4793  -13.5859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7386  -15.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6031  -12.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633  -14.8169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1846  -12.3522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540  -13.5871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3427  -14.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1870  -13.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0533  -14.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8874  -11.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7269  -11.9346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6806  -14.6597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8985  -14.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6800  -13.3267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4426  -13.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8937  -11.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0219  -13.1661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3097  -11.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7324  -13.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8982  -13.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 26  9  1  0
  2 29  2  0
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  5 28  2  0
  3  7  1  0
  8 25  2  0
 14  2  1  0
 12 15  1  0
  3 13  1  0
 27 14  2  0
 11 12  2  0
  4  1  1  0
 20 18  1  0
  2  5  1  0
 12 10  1  0
  6 21  2  0
 21 27  1  0
 19 16  1  0
 29  6  1  0
 25 31  1  0
 19 11  1  0
 20 17  1  1
 23  3  1  0
 24 23  1  0
 18  4  1  0
 16 27  1  0
 31 24  1  0
 30 26  2  0
 31 19  2  0
 28 30  1  0
 10 24  2  0
  9 22  2  0
 15 20  1  0
 23  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2295960

   (1R)-1-[[9-propan-2-yl-6-(3-pyrimidin-2-ylanilino)purin-2-yl]amino]butan-1-ol

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: 418.51

Molecular Weight (Monoisotopic): 418.2230

AlogP: 4.14

#Rotatable Bonds: 8

Polar Surface Area: 113.67

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: 3.62

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: -1.12

References

1. Demange L, Lozach O, Ferandin Y, Hoang NT, Meijer L, Galons H.  (2013)  Synthesis and evaluation of new potent inhibitors of CK1 and CDK5, two kinases involved in Alzheimers disease,  22  (7): [10.1007/s00044-012-0334-1]

Source

Source(1):

• Scientific Literature