2-{[(5-Isopropyl-3-methyl-1-benzothien-2-yl)sulfonyl]amino}-1,3-thiazole-5-carboxylic acid

ID: ALA3731045

PubChem CID: 56942934

Max Phase: Preclinical

Molecular Formula: C16H16N2O4S3

Molecular Weight: 396.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(S(=O)(=O)Nc2ncc(C(=O)O)s2)sc2ccc(C(C)C)cc12

Standard InChI:  InChI=1S/C16H16N2O4S3/c1-8(2)10-4-5-12-11(6-10)9(3)15(23-12)25(21,22)18-16-17-7-13(24-16)14(19)20/h4-8H,1-3H3,(H,17,18)(H,19,20)

Standard InChI Key:  VPYGNBKIDNDUGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    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
    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
   -2.7248    1.2135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955   -2.3548    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
   -5.1047    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7044   -1.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3047   -0.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    1.2992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3568    1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2191    2.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6447    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6416    0.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2141    0.0839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8501   -0.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7205   -1.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9482    0.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12  7  1  0
 12 13  2  0
 13  4  1  0
  9 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3731045

   2-[(3-Methyl-5-propan-2-yl-1-benzothiophen-2-yl)sulfonylamino]-1,3-thiazole-5-carboxylic 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: 396.51

Molecular Weight (Monoisotopic): 396.0272

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.26

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 0.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.35

References

1.  (2012)  New compounds, 

2.  (2016)  Sulfonamide compounds, 

Source

Source(2):

• BindingDB Database
• Patent Bioactivity Data