1,3-(Dihydroxyprop-2-yl)-6-[4-(5-pyrimidinyl)phenylamino]-9-iso-propylpurine

ID: ALA2295957

PubChem CID: 76334791

Max Phase: Preclinical

Molecular Formula: C21H24N8O2

Molecular Weight: 420.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1cnc2c(Nc3ccc(-c4cncnc4)cc3)nc(NC(O)CCO)nc21

Standard InChI:  InChI=1S/C21H24N8O2/c1-13(2)29-12-24-18-19(27-21(28-20(18)29)26-17(31)7-8-30)25-16-5-3-14(4-6-16)15-9-22-11-23-10-15/h3-6,9-13,17,30-31H,7-8H2,1-2H3,(H2,25,26,27,28)

Standard InChI Key:  AJLCOLFEZAFAFY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    8.1069  -20.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6590  -20.5323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6547  -18.0666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3728  -20.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0674  -16.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4864  -15.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9117  -16.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1548  -20.3700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5283  -19.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6572  -18.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2376  -20.5313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9482  -20.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1915  -15.1835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8169  -20.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9494  -19.2961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3725  -19.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9086  -15.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1076  -19.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5276  -20.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4059  -21.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0774  -18.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3617  -16.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8581  -21.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4912  -16.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088  -21.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6363  -19.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7840  -16.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2037  -16.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7861  -17.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1544  -19.0369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3680  -17.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  3  1  0
 13  6  2  0
  8 20  1  0
 16 10  2  0
 14  1  1  0
 27 24  1  0
  7 17  2  0
 20 25  1  0
 28  7  1  0
  3 31  1  0
 26 30  2  0
 12 11  1  0
 20 23  1  0
 12  2  1  0
 10 15  1  0
 16  4  1  0
  1 18  1  0
 27  5  1  0
  5 22  2  0
 21 29  1  0
  8 26  1  0
 11 19  1  0
 22 31  1  0
 19  9  1  0
 31 21  2  0
  6 24  1  0
 19 14  1  0
 17 13  1  0
  2  4  2  0
  4  8  1  0
 30 16  1  0
 29 27  2  0
 24 28  2  0
 15 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2295957

   1-[[9-Propan-2-yl-6-(4-pyrimidin-5-ylanilino)purin-2-yl]amino]propane-1,3-diol

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: 420.48

Molecular Weight (Monoisotopic): 420.2022

AlogP: 2.72

#Rotatable Bonds: 8

Polar Surface Area: 133.90

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.40

CX Basic pKa: 4.54

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: -0.73

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