Rac-N6-cis-(3-amino-5-chlorophenyl)-N2-(2-aminocyclohexyl)-9-isopropyl-9H-purine-2,6-diamine

ID: ALA4078898

PubChem CID: 134397387

Max Phase: Preclinical

Molecular Formula: C20H27ClN8

Molecular Weight: 414.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1cnc2c(Nc3cc(N)cc(Cl)c3)nc(N[C@@H]3CCCC[C@@H]3N)nc21

Standard InChI:  InChI=1S/C20H27ClN8/c1-11(2)29-10-24-17-18(25-14-8-12(21)7-13(22)9-14)27-20(28-19(17)29)26-16-6-4-3-5-15(16)23/h7-11,15-16H,3-6,22-23H2,1-2H3,(H2,25,26,27,28)/t15-,16+/m0/s1

Standard InChI Key:  ZYDSDRZMIWGATN-JKSUJKDBSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.8518  -10.4260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3360  -11.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8518  -11.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0787  -11.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3696  -11.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605  -11.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605  -10.6806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3696  -10.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0787  -10.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9555  -11.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3696   -9.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1064  -12.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5586  -13.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8980  -12.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464  -11.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5374  -11.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283  -11.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283  -10.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5374  -10.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464  -10.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5374  -12.7236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605   -9.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9555   -9.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464   -9.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464   -8.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9555   -7.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605   -8.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9555   -7.0033    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5374   -9.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
  6 10  1  0
  8 11  1  0
 12 13  1  0
 12 14  1  0
  3 12  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 16 21  1  1
 15 10  1  1
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 26 28  1  0
 24 29  1  0
 11 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4078898

   ---

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: 414.95

Molecular Weight (Monoisotopic): 414.2047

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 119.70

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.91

CX LogP: 3.28

CX LogD: 0.88

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.92

References

1. Shi Y, Park J, Lagisetti C, Zhou W, Sambucetti LC, Webb TR..  (2017)  A triple exon-skipping luciferase reporter assay identifies a new CLK inhibitor pharmacophore.,  27  (3): [PMID:28049589] [10.1016/j.bmcl.2016.12.056]

2. Shi Y, Park J, Lagisetti C, Zhou W, Sambucetti LC, Webb TR..  (2017)  A triple exon-skipping luciferase reporter assay identifies a new CLK inhibitor pharmacophore.,  27  (3): [PMID:28049589] [10.1016/j.bmcl.2016.12.056]

Source

Source(1):

• Scientific Literature