N-(2-Methoxybenzyl)-3-oxobenzo[d]isothiazole-2(3H)-carboxamide 1,1-Dioxide

ID: ALA5184346

PubChem CID: 168281731

Max Phase: Preclinical

Molecular Formula: C16H14N2O5S

Molecular Weight: 346.36

Names and Identifiers

Canonical SMILES:  COc1ccccc1CNC(=O)N1C(=O)c2ccccc2S1(=O)=O

Standard InChI:  InChI=1S/C16H14N2O5S/c1-23-13-8-4-2-6-11(13)10-17-16(20)18-15(19)12-7-3-5-9-14(12)24(18,21)22/h2-9H,10H2,1H3,(H,17,20)

Standard InChI Key:  REOVDRBXAOLCDP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.5866   -0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721   -0.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -1.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -1.7064    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -1.0390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182    0.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -1.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -0.3245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    0.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117    1.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007    2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -1.7535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721   -1.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866   -1.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -2.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  4  5  1  0
  5  6  1  0
  7  6  1  0
  3  7  1  0
  7  8  2  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  2  0
 13 14  1  0
 14 15  1  0
 16 13  1  0
 17 16  2  0
 18 17  1  0
 12 19  1  0
 19 18  2  0
  9 20  2  0
 21  4  1  0
  1 22  1  0
 22 21  2  0
  5 23  2  0
  5 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5184346

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.36

Molecular Weight (Monoisotopic): 346.0623

AlogP: 1.75

#Rotatable Bonds: 3

Polar Surface Area: 92.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.65

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: -1.12

References

1. Wen W, Cao H, Xu Y, Ren Y, Rao L, Shao X, Chen H, Wu L, Liu J, Su C, Peng C, Huang Y, Wan J..  (2022)  N-Acylamino Saccharin as an Emerging Cysteine-Directed Covalent Warhead and Its Application in the Identification of Novel FBPase Inhibitors toward Glucose Reduction.,  65  (13.0): [PMID:35786925] [10.1021/acs.jmedchem.2c00336]

Source

Source(1):

• Scientific Literature