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

ID: ALA5200188

PubChem CID: 168290735

Max Phase: Preclinical

Molecular Formula: C15H11FN2O4S

Molecular Weight: 334.33

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1F)N1C(=O)c2ccccc2S1(=O)=O

Standard InChI:  InChI=1S/C15H11FN2O4S/c16-12-7-3-1-5-10(12)9-17-15(20)18-14(19)11-6-2-4-8-13(11)23(18,21)22/h1-8H,9H2,(H,17,20)

Standard InChI Key:  PVAQEKOYPDHKAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.2057   -0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -1.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -1.3634    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -0.6959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370    0.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    0.0185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555    0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    0.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555    1.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    1.4475    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931    2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2057    1.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931    0.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -1.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912   -1.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057   -1.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -2.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -1.9476    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
 15 13  1  0
 16 15  2  0
 17 16  1  0
 12 18  1  0
 18 17  2  0
  9 19  2  0
 20  4  1  0
  1 21  1  0
 21 20  2  0
  5 22  2  0
  5 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5200188

   ---

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: 334.33

Molecular Weight (Monoisotopic): 334.0424

AlogP: 1.88

#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: 11.45

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.91

Np Likeness Score: -1.59

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