2-[(9-Isopropyl-2-piperazin-1-yl-9H-purin-6-ylamino)-methyl]-6-methoxyphenol

ID: ALA2349191

PubChem CID: 71579158

Max Phase: Preclinical

Molecular Formula: C20H27N7O2

Molecular Weight: 397.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2nc(N3CCNCC3)nc3c2ncn3C(C)C)c1O

Standard InChI:  InChI=1S/C20H27N7O2/c1-13(2)27-12-23-16-18(22-11-14-5-4-6-15(29-3)17(14)28)24-20(25-19(16)27)26-9-7-21-8-10-26/h4-6,12-13,21,28H,7-11H2,1-3H3,(H,22,24,25)

Standard InChI Key:  WNGBFCDSTYVCFL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   20.5112   -6.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2987   -6.5870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5112   -5.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7946   -6.7496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2987   -5.2497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0821   -5.5080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0821   -6.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7946   -5.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7862   -5.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7863   -4.2706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3614   -6.7496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5570   -7.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5070   -3.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4988   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9987   -7.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3611   -7.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7821   -2.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2070   -2.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1986   -1.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7737   -1.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4862   -1.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0729   -3.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0570   -1.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0524   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6439   -6.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9253   -6.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9178   -7.5691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6352   -7.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3601   -7.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  3  1  0
  6  7  2  0
  7  4  1  0
  8  3  2  0
  9  2  1  0
 10  8  1  0
 11  7  1  0
 12  2  1  0
 13 10  1  0
 14 13  1  0
 15 12  1  0
 16 12  1  0
 17 14  2  0
 18 14  1  0
 19 18  2  0
 20 17  1  0
 21 19  1  0
  8  6  1  0
  9  5  2  0
 20 21  2  0
 17 22  1  0
 20 23  1  0
 23 24  1  0
 11 25  1  0
 11 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2349191

   2-Methoxy-6-[[(2-piperazin-1-yl-9-propan-2-ylpurin-6-yl)amino]methyl]phenol

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: 397.48

Molecular Weight (Monoisotopic): 397.2226

AlogP: 2.14

#Rotatable Bonds: 6

Polar Surface Area: 100.36

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.73

CX Basic pKa: 8.65

CX LogP: 2.03

CX LogD: 0.97

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -0.91

References

1. Zatloukal M, Jorda R, Gucký T, Řezníčková E, Voller J, Pospíšil T, Malínková V, Adamcová H, Kryštof V, Strnad M..  (2013)  Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases.,  61  [PMID:22770608] [10.1016/j.ejmech.2012.06.036]

Source

Source(1):

• Scientific Literature