(4-{4-Amino-1-[4-(4-methyl-piperazin-1-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxy-phenyl)-carbamic acid benzyl ester

ID: ALA47787

Chembl Id: CHEMBL47787

PubChem CID: 6539957

Max Phase: Preclinical

Molecular Formula: C31H38N8O3

Molecular Weight: 570.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nn([C@H]3CC[C@H](N4CCN(C)CC4)CC3)c3ncnc(N)c23)ccc1NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C31H38N8O3/c1-37-14-16-38(17-15-37)23-9-11-24(12-10-23)39-30-27(29(32)33-20-34-30)28(36-39)22-8-13-25(26(18-22)41-2)35-31(40)42-19-21-6-4-3-5-7-21/h3-8,13,18,20,23-24H,9-12,14-17,19H2,1-2H3,(H,35,40)(H2,32,33,34)/t23-,24-

Standard InChI Key:  LGMDJFPPNVPECO-RQNOJGIXSA-N

Alternative Forms

1. Parent:

   

   ALA47787

   Pyrazolo[3,4-d]pyrimidine 6

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: 570.70

Molecular Weight (Monoisotopic): 570.3067

AlogP: 4.56

#Rotatable Bonds: 7

Polar Surface Area: 123.66

Molecular Species: BASE

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.13

CX Basic pKa: 8.82

CX LogP: 4.05

CX LogD: 2.62

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.33

Np Likeness Score: -1.10

References

1. Burchat AF, Calderwood DJ, Friedman MM, Hirst GC, Li B, Rafferty P, Ritter K, Skinner BS..  (2002)  Pyrazolo[3,4-d]pyrimidines containing an extended 3-substituent as potent inhibitors of Lck -- a selectivity insight.,  12  (12): [PMID:12039591] [10.1016/s0960-894x(02)00196-8]

2. Borhani DW, Calderwood DJ, Friedman MM, Hirst GC, Li B, Leung AK, McRae B, Ratnofsky S, Ritter K, Waegell W..  (2004)  A-420983: a potent, orally active inhibitor of lck with efficacy in a model of transplant rejection.,  14  (10): [PMID:15109663] [10.1016/j.bmcl.2004.02.101]

Source

Source(1):

• Scientific Literature