4-chloro-2-(3-(4-chlorophenylsulfonamido)quinoxalin-2-ylamino)benzoic acid

ID: ALA2299388

PubChem CID: 1871291

Max Phase: Preclinical

Molecular Formula: C21H14Cl2N4O4S

Molecular Weight: 489.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(Cl)cc1Nc1nc2ccccc2nc1NS(=O)(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H14Cl2N4O4S/c22-12-5-8-14(9-6-12)32(30,31)27-20-19(24-16-3-1-2-4-17(16)25-20)26-18-11-13(23)7-10-15(18)21(28)29/h1-11H,(H,24,26)(H,25,27)(H,28,29)

Standard InChI Key:  KDRUERVLJQMQQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   19.9042   -5.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9031   -5.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6152   -6.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3290   -5.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3262   -5.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6134   -4.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0374   -6.2700    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.1896   -4.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1894   -3.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4778   -5.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6110   -3.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3216   -3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0284   -3.8032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0185   -2.1605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3155   -2.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7366   -2.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7385   -3.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4488   -3.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1578   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1519   -2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4410   -2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6007   -2.1694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5948   -1.3481    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.8800   -0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8761   -0.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1622    0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4523   -0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4609   -0.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1754   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7370    0.2743    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.3832   -1.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1686   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  8  9  1  0
  8 10  2  0
  1  8  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 13 17  1  0
 16 14  1  0
 14 15  2  0
 15 12  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
 15 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
 23 31  2  0
 23 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2299388

   4-Chloro-2-[[3-[(4-chlorophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid

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: 489.34

Molecular Weight (Monoisotopic): 488.0113

AlogP: 5.18

#Rotatable Bonds: 6

Polar Surface Area: 121.28

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.60

CX Basic pKa: ┄

CX LogP: 6.58

CX LogD: 2.42

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -1.34

References

1. Park H, Kyung A, Lee H, Kang S, Yoon T, Ryu SE, Jeong DG.  (2013)  Virtual screening and biochemical evaluation of the inhibitors of dual-specificity phosphatase 26,  22  (8): [10.1007/s00044-012-0405-3]

Source

Source(1):

• Scientific Literature