N-(4-{4-Amino-1-[4-(4-methyl-piperazin-1-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxy-phenyl)-benzamide

ID: ALA297363

Chembl Id: CHEMBL297363

PubChem CID: 6539956

Max Phase: Preclinical

Molecular Formula: C30H36N8O2

Molecular Weight: 540.67

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)c1ccccc1

Standard InChI:  InChI=1S/C30H36N8O2/c1-36-14-16-37(17-15-36)22-9-11-23(12-10-22)38-29-26(28(31)32-19-33-29)27(35-38)21-8-13-24(25(18-21)40-2)34-30(39)20-6-4-3-5-7-20/h3-8,13,18-19,22-23H,9-12,14-17H2,1-2H3,(H,34,39)(H2,31,32,33)/t22-,23-

Standard InChI Key:  OKRHYXZXYNXSAO-YHBQERECSA-N

Alternative Forms

1. Parent:

   

   ALA297363

   Pyrazolo[3,4-d]pyrimidine 5

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: 540.67

Molecular Weight (Monoisotopic): 540.2961

AlogP: 4.07

#Rotatable Bonds: 6

Polar Surface Area: 114.43

Molecular Species: BASE

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 3.57

CX LogD: 2.13

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.38

Np Likeness Score: -1.22

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]

3. Curtin ML, Frey RR, Heyman HR, Sarris KA, Steinman DH, Holmes JH, Bousquet PF, Cunha GA, Moskey MD, Ahmed AA, Pease LJ, Glaser KB, Stewart KD, Davidsen SK, Michaelides MR..  (2004)  Isoindolinone ureas: a novel class of KDR kinase inhibitors.,  14  (17): [PMID:15357981] [10.1016/j.bmcl.2004.06.041]

Source

Source(1):

• Scientific Literature