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

ID: ALA2272851

PubChem CID: 76327040

Max Phase: Preclinical

Molecular Formula: C17H18ClNO4S

Molecular Weight: 367.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)c1cc(-n2c(=O)c3c([s+]2[O-])CCCC3)ccc1Cl

Standard InChI:  InChI=1S/C17H18ClNO4S/c1-10(2)23-17(21)13-9-11(7-8-14(13)18)19-16(20)12-5-3-4-6-15(12)24(19)22/h7-10H,3-6H2,1-2H3

Standard InChI Key:  AKIYRAVGZMIZBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.5661  -21.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443  -21.4555    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968  -22.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8253  -20.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609  -21.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5662  -20.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556  -21.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609  -19.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444  -20.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556  -20.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969  -19.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415  -20.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0495  -21.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473  -20.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659  -21.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624  -20.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2754  -20.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2742  -22.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925  -20.7938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8652  -22.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0914  -22.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4996  -22.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0907  -23.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3168  -22.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  2  4  1  0
  5  1  1  0
  6  1  2  0
  7  5  1  0
  6  8  1  0
  9  6  1  0
 10  7  1  0
 10  8  1  0
  4  9  1  0
  9 11  2  0
  4 12  1  0
 12 13  2  0
 14 12  1  0
 13 15  1  0
 16 14  2  0
 15 17  2  0
 15 18  1  0
 17 16  1  0
 17 19  1  0
 18 20  2  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
M  CHG  2   2   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2272851

   Propan-2-yl 2-chloro-5-(1,3-dioxo-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: 367.85

Molecular Weight (Monoisotopic): 367.0645

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 71.36

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.21

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.93

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