N-(4-Ethynylbenzyl)-3-oxobenzo[d]isothiazole-2(3H)-carboxamide 1,1-Dioxide

ID: ALA5204561

PubChem CID: 168295105

Max Phase: Preclinical

Molecular Formula: C17H12N2O4S

Molecular Weight: 340.36

Names and Identifiers

Canonical SMILES:  C#Cc1ccc(CNC(=O)N2C(=O)c3ccccc3S2(=O)=O)cc1

Standard InChI:  InChI=1S/C17H12N2O4S/c1-2-12-7-9-13(10-8-12)11-18-17(21)19-16(20)14-5-3-4-6-15(14)24(19,22)23/h1,3-10H,11H2,(H,18,21)

Standard InChI Key:  ATJDZKUBZKZWLW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -3.8235    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946   -0.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -0.9922    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -0.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    0.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1122    0.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1122   -1.0391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8235   -0.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -1.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959   -1.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9374    0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9374    1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876    3.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    3.9621    0.0000 C   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
  9 11  2  0
 12  4  1  0
  1 13  1  0
 13 12  2  0
  5 14  2  0
  5 15  2  0
 10 16  1  0
 16 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 17 18  2  0
 22 17  1  0
 20 23  1  0
 23 24  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5204561

   ---

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: 340.36

Molecular Weight (Monoisotopic): 340.0518

AlogP: 1.72

#Rotatable Bonds: 2

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.65

CX Basic pKa: ┄

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -1.30

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