2-Chloro-5-(1,1,3-trioxo-1,3,4,5,6,7-hexahydro-1lambda*6*-benzo[d]isothiazol-2-yl)-benzoic acid isopropyl ester

ID: ALA2272852

PubChem CID: 76327041

Max Phase: Preclinical

Molecular Formula: C17H18ClNO5S

Molecular Weight: 383.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)c1cc(N2C(=O)C3=C(CCCC3)S2(=O)=O)ccc1Cl

Standard InChI:  InChI=1S/C17H18ClNO5S/c1-10(2)24-17(21)13-9-11(7-8-14(13)18)19-16(20)12-5-3-4-6-15(12)25(19,22)23/h7-10H,3-6H2,1-2H3

Standard InChI Key:  JRHFWWNBUNIGPF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.2338  -22.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0502  -22.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4597  -21.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467  -20.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2316  -20.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2768  -21.6151    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -23.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0495  -23.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2757  -23.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6839  -23.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2750  -24.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5011  -23.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5252  -22.2809    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3552  -23.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1325  -22.8278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3399  -21.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3399  -22.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0452  -22.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0452  -20.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7505  -21.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7504  -22.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0096  -21.6149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5287  -20.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7812  -20.1758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8233  -21.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 25  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 25  1  0
  3  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 14 13  2  0
 13 15  2  0
 16 17  1  0
 16 19  1  0
 17 18  1  0
 18 21  1  0
 20 19  1  0
 20 21  2  0
 21 13  1  0
 13 22  1  0
 22 23  1  0
 23 20  1  0
 23 24  2  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272852

   Propan-2-yl 2-chloro-5-(1,1,3-trioxo-4,5,6,7-tetrahydro-1,2-benzothiazol-2-yl)benzoate

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: 383.85

Molecular Weight (Monoisotopic): 383.0594

AlogP: 3.41

#Rotatable Bonds: 3

Polar Surface Area: 80.75

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.04

References

1. MIYAMOTO Y, IKEDA Y, WAKABAYASHI K.  (2003)  Synthesis and Phytotoxic Activities of N-Substituted Phenyl Isothiazolone Derivatives,  28  (3): [10.1584/jpestics.28.293]

Source

Source(1):

• Scientific Literature