(R)-N6-(3-amino-5-chlorophenyl)-9-isopropyl-N2-(pyrrolidin-3-yl)-9H-purine-2,6-diamine

ID: ALA4084116

PubChem CID: 134397798

Max Phase: Preclinical

Molecular Formula: C18H23ClN8

Molecular Weight: 386.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1cnc2c(Nc3cc(N)cc(Cl)c3)nc(N[C@@H]3CCNC3)nc21

Standard InChI:  InChI=1S/C18H23ClN8/c1-10(2)27-9-22-15-16(23-14-6-11(19)5-12(20)7-14)25-18(26-17(15)27)24-13-3-4-21-8-13/h5-7,9-10,13,21H,3-4,8,20H2,1-2H3,(H2,23,24,25,26)/t13-/m1/s1

Standard InChI Key:  GPXCDUCDIFDAGL-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   13.9242  -10.5405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4088  -11.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9242  -11.8754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1395  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280  -12.0349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7122  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7122  -10.7976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280  -10.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1395  -10.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9964  -12.0349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280   -9.5602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3898  -10.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1958  -10.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2805  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5303  -11.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9773  -11.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1812  -12.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9761  -12.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5974  -13.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7122   -9.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9964   -9.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2805   -9.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2805   -8.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9964   -7.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7122   -8.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9964   -7.0854    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5689   -9.5602    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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 16  1  0
 14 10  1  6
 17 18  1  0
 17 19  1  0
  3 17  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 24 26  1  0
 22 27  1  0
 11 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084116

   ---

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: 386.89

Molecular Weight (Monoisotopic): 386.1734

AlogP: 3.16

#Rotatable Bonds: 5

Polar Surface Area: 105.71

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.29

CX LogP: 2.25

CX LogD: -0.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -1.12

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]

Source

Source(1):

• Scientific Literature