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

ID: ALA5207512

PubChem CID: 168297671

Max Phase: Preclinical

Molecular Formula: C16H14N2O5S

Molecular Weight: 346.36

Names and Identifiers

Canonical SMILES:  COc1cccc(CNC(=O)N2C(=O)c3ccccc3S2(=O)=O)c1

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

Standard InChI Key:  GUCAKADRDVCUDM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.5867   -0.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8722   -0.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.0637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -1.3962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -0.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    0.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -0.6818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    0.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    1.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    2.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117    2.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742    2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867    1.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742    0.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -2.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8722   -2.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731   -2.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -2.4763    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
 14 13  1  0
 14 15  1  0
 15 16  1  0
 17 14  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:

   

   ALA5207512

   ---

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: 11.70

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: -1.17

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