1-(cyclopentylmethyl)-N-methyl-3-[6-(piperazin-1-yl)pyridin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-amine

ID: ALA4213003

PubChem CID: 145965329

Max Phase: Preclinical

Molecular Formula: C21H28N8

Molecular Weight: 392.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ncc2c(-c3ccc(N4CCNCC4)nc3)nn(CC3CCCC3)c2n1

Standard InChI:  InChI=1S/C21H28N8/c1-22-21-25-13-17-19(27-29(20(17)26-21)14-15-4-2-3-5-15)16-6-7-18(24-12-16)28-10-8-23-9-11-28/h6-7,12-13,15,23H,2-5,8-11,14H2,1H3,(H,22,25,26)

Standard InChI Key:  MMJWZGGVKOHMPQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    3.1152   -5.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1141   -6.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8289   -7.1278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -5.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426   -5.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5474   -6.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -6.9612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8169   -6.2898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271   -5.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994   -7.1269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -6.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5944   -7.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0460   -8.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248   -8.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936   -9.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -9.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219   -9.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -4.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -4.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356   -3.8812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0798   -3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702   -3.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0235   -4.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339   -2.4873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1409   -2.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3910   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8375   -0.9248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0304   -1.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769   -1.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  9 18  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213003

   ---

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: 392.51

Molecular Weight (Monoisotopic): 392.2437

AlogP: 2.53

#Rotatable Bonds: 5

Polar Surface Area: 83.79

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 2.67

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.66

References

1. Myers SH, Temps C, Houston DR, Brunton VG, Unciti-Broceta A..  (2018)  Development of Potent Inhibitors of Receptor Tyrosine Kinases by Ligand-Based Drug Design and Target-Biased Phenotypic Screening.,  61  (5): [PMID:29466002] [10.1021/acs.jmedchem.7b01605]

Source

Source(1):

• Scientific Literature