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

ID: ALA3360056

PubChem CID: 118724033

Max Phase: Preclinical

Molecular Formula: C18H17NO3S

Molecular Weight: 327.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCCC(=O)n2sc3ccccc3c2=O)cc1

Standard InChI:  InChI=1S/C18H17NO3S/c1-22-14-11-9-13(10-12-14)5-4-8-17(20)19-18(21)15-6-2-3-7-16(15)23-19/h2-3,6-7,9-12H,4-5,8H2,1H3

Standard InChI Key:  YZQKWJFJWRAGSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.8197   -8.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8197   -9.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5273   -9.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2392   -9.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2392   -8.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5273   -7.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0205   -8.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5049   -8.7381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0205   -9.3993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.3235   -8.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7306   -8.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7306   -9.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5491   -9.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9603  -10.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7817  -10.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1903  -10.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0116  -10.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4243  -10.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0116   -9.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1903   -9.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2428  -10.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6500   -9.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2763   -7.2943    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
 21 22  1  0
  7 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360056

   ---

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: 327.41

Molecular Weight (Monoisotopic): 327.0929

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 48.30

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: -0.66

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