2-(4-(2,3-Dichlorophenylsulfonamido)-3-methoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid

ID: ALA4088207

PubChem CID: 137643926

Max Phase: Preclinical

Molecular Formula: C14H11Cl2N5O5S

Molecular Weight: 432.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nn(CC(=O)O)c2ncnc(NS(=O)(=O)c3cccc(Cl)c3Cl)c12

Standard InChI:  InChI=1S/C14H11Cl2N5O5S/c1-26-14-10-12(17-6-18-13(10)21(19-14)5-9(22)23)20-27(24,25)8-4-2-3-7(15)11(8)16/h2-4,6H,5H2,1H3,(H,22,23)(H,17,18,20)

Standard InChI Key:  NKFFHONHDOSSTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   30.1245  -12.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5388  -11.3090    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.7130  -11.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2564  -11.7176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5402  -10.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2553  -10.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2543   -9.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5378   -8.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8210   -9.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8256  -10.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7406  -12.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7366  -14.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2244  -13.3721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9522  -13.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9585  -12.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2509  -12.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5365  -12.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5342  -13.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2424  -14.1860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9958  -11.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1137  -10.4970    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.1037   -8.8459    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.8037  -11.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9890  -14.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7961  -14.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0484  -15.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3510  -14.3877    0.0000 O   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
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088207

   ---

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: 432.25

Molecular Weight (Monoisotopic): 430.9858

AlogP: 2.03

#Rotatable Bonds: 6

Polar Surface Area: 136.30

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.57

CX Basic pKa: 0.30

CX LogP: 2.07

CX LogD: -2.33

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -1.67

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