(S)-2-(1-Hydroxy-4-methylpent-2-ylamino)-6-[4-(5-pyrimidinyl)phenylamino]-9-iso-propylpurine

ID: ALA2295956

PubChem CID: 76320343

Max Phase: Preclinical

Molecular Formula: C24H30N8O

Molecular Weight: 446.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CC[C@H](O)Nc1nc(Nc2ccc(-c3cncnc3)cc2)c2ncn(C(C)C)c2n1

Standard InChI:  InChI=1S/C24H30N8O/c1-15(2)5-10-20(33)29-24-30-22(21-23(31-24)32(14-27-21)16(3)4)28-19-8-6-17(7-9-19)18-11-25-13-26-12-18/h6-9,11-16,20,33H,5,10H2,1-4H3,(H2,28,29,30,31)/t20-/m0/s1

Standard InChI Key:  ZWHTWAOLEGXRTP-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   24.3425  -18.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5192  -21.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3445  -19.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4547  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9718  -22.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6903  -21.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4578  -18.1179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1948  -21.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5203  -20.9828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7088  -20.7237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9265  -19.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4207  -23.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7092  -22.0526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7416  -16.8911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1074  -20.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4002  -22.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9725  -23.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9643  -22.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9311  -20.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2215  -19.7617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1068  -21.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9313  -21.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6400  -19.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8127  -22.2139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2257  -22.2148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7538  -18.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2239  -20.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0455  -18.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7631  -23.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9202  -18.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2693  -21.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0407  -17.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6300  -18.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21 15  1  6
 19 22  1  0
 22 13  1  0
  5 17  1  0
  5 31  1  0
  8 10  2  0
 19 27  2  0
  7  4  2  0
 10 19  1  0
  4 14  1  0
 20 11  1  0
 14 32  2  0
 18 29  1  0
 13  8  1  0
  9  2  2  0
 27  9  1  0
 23  3  1  0
 18 12  1  0
  2 25  1  0
 21 16  1  0
  1 28  1  0
  6  5  1  0
  3  1  2  0
  1 33  1  0
 27 20  1  0
 16  6  1  0
 26  7  1  0
 32 28  1  0
 33 30  2  0
 13 18  1  0
 30 11  1  0
 25 22  2  0
 24 21  1  0
  2 24  1  0
 11 23  2  0
 28 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2295956

   (1S)-4-methyl-1-[[9-propan-2-yl-6-(4-pyrimidin-5-ylanilino)purin-2-yl]amino]pentan-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: 446.56

Molecular Weight (Monoisotopic): 446.2543

AlogP: 4.77

#Rotatable Bonds: 9

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: 3.64

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.75

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