2-(4-(p-Tolyl)butanoyl)benzo[d]isothiazol-3(2H)-one

ID: ALA3360055

PubChem CID: 118724032

Max Phase: Preclinical

Molecular Formula: C18H17NO2S

Molecular Weight: 311.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCCC(=O)n2sc3ccccc3c2=O)cc1

Standard InChI:  InChI=1S/C18H17NO2S/c1-13-9-11-14(12-10-13)5-4-8-17(20)19-18(21)15-6-2-3-7-16(15)22-19/h2-3,6-7,9-12H,4-5,8H2,1H3

Standard InChI Key:  GTXNLQVCIHMROL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.1385   -7.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385   -8.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780   -8.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -8.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -7.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780   -6.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0710   -7.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515   -7.7187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0710   -8.3799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699   -7.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -7.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -8.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5997   -8.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0069   -9.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282   -9.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2409   -9.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0622   -9.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4708   -9.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0622   -8.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2409   -8.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2893   -9.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3227   -6.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  5  1  0
  8  7  1  0
  9  8  1  0
  4  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  7 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360055

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 311.41

Molecular Weight (Monoisotopic): 311.0980

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 39.07

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.81

References

1. Li Z, Pan Y, Zhong W, Zhu Y, Zhao Y, Li L, Liu W, Zhou H, Yang C..  (2014)  Synthesis and evaluation of N-acyl-substituted 1,2-benzisothiazol-3-one derivatives as caspase-3 inhibitors.,  22  (24): [PMID:25468037] [10.1016/j.bmc.2014.11.005]

Source

Source(1):

• Scientific Literature