3-oxo-N-(1-phenylethyl)benzo[d]isothiazole-2(3H)-carboxamide 1,1-Dioxide

ID: ALA5195989

PubChem CID: 168286734

Max Phase: Preclinical

Molecular Formula: C16H14N2O4S

Molecular Weight: 330.37

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(NC(=O)N1C(=O)c2ccccc2S1(=O)=O)c1ccccc1

Standard InChI:  InChI=1S/C16H14N2O4S/c1-11(12-7-3-2-4-8-12)17-16(20)18-15(19)13-9-5-6-10-14(13)23(18,21)22/h2-11H,1H3,(H,17,20)

Standard InChI Key:  BXHRLCQUYVVCIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.2055    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4910    0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -0.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9919   -0.6463    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9919    0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370    1.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304    0.7355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    0.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9679    1.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9679    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055   -0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9679   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4910   -0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -0.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9919   -1.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -1.0597    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
 11 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 13 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:

    ALA5195989

    ---

Associated Targets(Human)

FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 330.37Molecular Weight (Monoisotopic): 330.0674AlogP: 2.30#Rotatable Bonds: 2
Polar Surface Area: 83.55Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 11.65CX Basic pKa: CX LogP: 2.47CX LogD: 2.47
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.92Np Likeness Score: -1.09

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