(R)-2-[6-(4-Aminobenzylamino)-9-isopropyl-9H-purin-2-ylamino]-butan-1-ol

ID: ALA2347579

PubChem CID: 71579001

Max Phase: Preclinical

Molecular Formula: C19H27N7O

Molecular Weight: 369.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](CO)Nc1nc(NCc2ccc(N)cc2)c2ncn(C(C)C)c2n1

Standard InChI:  InChI=1S/C19H27N7O/c1-4-15(10-27)23-19-24-17(21-9-13-5-7-14(20)8-6-13)16-18(25-19)26(11-22-16)12(2)3/h5-8,11-12,15,27H,4,9-10,20H2,1-3H3,(H2,21,23,24,25)/t15-/m1/s1

Standard InChI Key:  CATARZWLWHJIHA-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   20.5290   -5.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3180   -6.0957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5290   -5.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8108   -6.2585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3180   -4.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0968   -5.0143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0968   -5.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8108   -4.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8065   -5.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8024   -3.7743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3746   -6.2585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5769   -6.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5248   -3.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5164   -2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6607   -5.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2328   -5.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0175   -7.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3827   -7.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9467   -6.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7983   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2262   -2.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6607   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9342   -4.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2179   -1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7900   -1.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5039   -0.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5021   -0.0710    0.0000 N   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 11  1  0
 16 19  1  0
 17 12  1  0
 18 12  1  0
 19 15  1  0
 20 14  2  0
 21 14  1  0
 15 22  1  1
 23 22  1  0
 24 21  2  0
 25 20  1  0
 26 24  1  0
  8  6  1  0
  9  5  2  0
 25 26  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2347579

   (2R)-2-[[6-[(4-aminophenyl)methylamino]-9-propan-2-ylpurin-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: 369.47

Molecular Weight (Monoisotopic): 369.2277

AlogP: 2.78

#Rotatable Bonds: 8

Polar Surface Area: 113.91

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.24

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.67

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