(R)-2-(9-cyclopentyl-6-(4-(pyridin-2-yl)benzylamino)-9H-purin-2-ylamino)butan-1-ol

ID: ALA2402949

PubChem CID: 73347509

Max Phase: Preclinical

Molecular Formula: C26H31N7O

Molecular Weight: 457.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](CO)Nc1nc(NCc2ccc(-c3ccccn3)cc2)c2ncn(C3CCCC3)c2n1

Standard InChI:  InChI=1S/C26H31N7O/c1-2-20(16-34)30-26-31-24(23-25(32-26)33(17-29-23)21-7-3-4-8-21)28-15-18-10-12-19(13-11-18)22-9-5-6-14-27-22/h5-6,9-14,17,20-21,34H,2-4,7-8,15-16H2,1H3,(H2,28,30,31,32)/t20-/m1/s1

Standard InChI Key:  FLIJBHQHRINPMX-HXUWFJFHSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   15.4448   -8.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2323   -8.6286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4448   -7.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7283   -8.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2323   -7.2913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0158   -7.5495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0158   -8.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7283   -7.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7198   -7.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7199   -6.3122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2950   -8.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4907   -9.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407   -5.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4324   -5.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5825   -8.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1576   -8.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5825   -7.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8576   -7.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1323   -3.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7074   -3.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4199   -3.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0054  -10.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944  -10.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2819  -10.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2796   -9.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4199   -2.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1351   -2.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1336   -1.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4178   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7018   -1.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7069   -2.2117    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 11  1  0
 16 17  1  0
 17 15  1  0
 18 14  2  0
 19 14  1  0
 15 20  1  1
 21 20  1  0
 22 19  2  0
 23 18  1  0
 24 22  1  0
  8  6  1  0
  9  5  2  0
 23 24  2  0
 27 28  1  0
 25 26  1  0
 12 25  1  0
 26 27  1  0
 28 12  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2402949

   (2R)-2-[[9-cyclopentyl-6-[(4-pyridin-2-ylphenyl)methylamino]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: 457.58

Molecular Weight (Monoisotopic): 457.2590

AlogP: 4.80

#Rotatable Bonds: 9

Polar Surface Area: 100.78

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.26

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.82

References

1. Gucký T, Jorda R, Zatloukal M, Bazgier V, Berka K, Řezníčková E, Béres T, Strnad M, Kryštof V..  (2013)  A novel series of highly potent 2,6,9-trisubstituted purine cyclin-dependent kinase inhibitors.,  56  (15): [PMID:23829517] [10.1021/jm4006884]

Source

Source(1):

• Scientific Literature