3-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid

ID: ALA3728731

Cas Number: 1365719-41-0

PubChem CID: 56941306

Max Phase: Preclinical

Molecular Formula: C16H12ClNO4S2

Molecular Weight: 381.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(S(=O)(=O)Nc2cccc(C(=O)O)c2)sc2ccc(Cl)cc12

Standard InChI:  InChI=1S/C16H12ClNO4S2/c1-9-13-8-11(17)5-6-14(13)23-16(9)24(21,22)18-12-4-2-3-10(7-12)15(19)20/h2-8,18H,1H3,(H,19,20)

Standard InChI Key:  NFLZAWLLXDSRBZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -0.4916   -3.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -4.4208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -4.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529   -5.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -5.7210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -7.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059   -8.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5586   -9.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586   -9.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8059   -8.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533   -7.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3067   -8.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9031   -7.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9107   -9.3461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  2  1  0
 11  5  1  0
  3 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728731

   3-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]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: 381.86

Molecular Weight (Monoisotopic): 380.9896

AlogP: 4.36

#Rotatable Bonds: 4

Polar Surface Area: 83.47

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.96

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 0.40

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -1.51

References

1.  (2012)  New compounds, 

2.  (2016)  Sulfonamide compounds, 

3. Wang Y, Qu C, Liu T, Wang C..  (2020)  PFKFB3 inhibitors as potential anticancer agents: Mechanisms of action, current developments, and structure-activity relationships.,  203  [PMID:32679452] [10.1016/j.ejmech.2020.112612]

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data