N-(6-Amino-3-methoxy-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-2,3-dichlorobenzenesulfonamide

ID: ALA4089151

PubChem CID: 137644457

Max Phase: Preclinical

Molecular Formula: C13H12Cl2N6O3S

Molecular Weight: 403.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nn(C)c2nc(N)nc(NS(=O)(=O)c3cccc(Cl)c3Cl)c12

Standard InChI:  InChI=1S/C13H12Cl2N6O3S/c1-21-11-8(12(19-21)24-2)10(17-13(16)18-11)20-25(22,23)7-5-3-4-6(14)9(7)15/h3-5H,1-2H3,(H3,16,17,18,20)

Standard InChI Key:  XTBTVGBOOSJBMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   30.1757  -12.8793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5903  -12.1645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.7639  -12.1628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3084  -12.5735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5917  -11.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3073  -10.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3063  -10.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5893   -9.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8720  -10.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8765  -10.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7935  -13.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7897  -14.8959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2778  -14.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0046  -14.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0110  -13.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3028  -13.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5880  -13.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5856  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2943  -15.0435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0491  -12.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1641  -11.3519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.1541   -9.6997    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.8575  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0422  -15.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8689  -15.0437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 15  1  0
 14 12  1  0
 12 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16  4  1  0
 11 20  1  0
 10 21  1  0
  9 22  1  0
 20 23  1  0
 12 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089151

   ---

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: 403.25

Molecular Weight (Monoisotopic): 402.0069

AlogP: 2.06

#Rotatable Bonds: 4

Polar Surface Area: 125.02

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.59

CX Basic pKa: 0.32

CX LogP: 2.44

CX LogD: 1.55

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.93

References

1. Miah AH, Champigny AC, Graves RH, Hodgson ST, Percy JM, Procopiou PA..  (2017)  Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists.,  25  (20): [PMID:28801066] [10.1016/j.bmc.2017.07.052]

Source

Source(1):

• Scientific Literature