Rac-N-cis(3-((2-((2-aminocyclohexyl)amino)-9-isopropyl-9H-purin-6-yl)amino)-5-chlorophenyl)acetamide

ID: ALA4094492

PubChem CID: 134397388

Max Phase: Preclinical

Molecular Formula: C22H29ClN8O

Molecular Weight: 456.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(Cl)cc(Nc2nc(N[C@@H]3CCCC[C@@H]3N)nc3c2ncn3C(C)C)c1

Standard InChI:  InChI=1S/C22H29ClN8O/c1-12(2)31-11-25-19-20(27-16-9-14(23)8-15(10-16)26-13(3)32)29-22(30-21(19)31)28-18-7-5-4-6-17(18)24/h8-12,17-18H,4-7,24H2,1-3H3,(H,26,32)(H2,27,28,29,30)/t17-,18+/m0/s1

Standard InChI Key:  ZYFRJAWGLQYBTJ-ZWKOTPCHSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   35.8088  -20.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8169  -19.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0958  -20.8244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5096  -20.8444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4975  -21.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2024  -22.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1902  -22.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4772  -23.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7764  -22.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7844  -22.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0633  -23.2756    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.8952  -23.3156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3660  -24.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8370  -24.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3479  -25.6302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5758  -25.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8628  -25.7669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1578  -25.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1700  -24.5313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8830  -24.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5839  -24.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5911  -26.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3783  -26.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0054  -26.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4448  -25.7469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7439  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0309  -25.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3301  -25.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3381  -24.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0512  -24.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7561  -24.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0187  -26.5440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  9 11  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13 21  1  0
 16 21  1  0
 22 23  1  0
 22 24  1  0
 15 22  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 26 31  1  0
 27 32  1  1
 26 25  1  1
 18 25  1  0
 12 20  1  0
  7 12  1  0
  4  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094492

   ---

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: 456.98

Molecular Weight (Monoisotopic): 456.2153

AlogP: 4.44

#Rotatable Bonds: 6

Polar Surface Area: 122.78

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.56

CX Basic pKa: 9.91

CX LogP: 3.35

CX LogD: 0.95

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -1.17

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