Methanesulfonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

ID: ALA142025

Cas Number: 57212-70-1

PubChem CID: 262936

Max Phase: Preclinical

Molecular Formula: C9H7NO5S

Molecular Weight: 241.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)ON1C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C9H7NO5S/c1-16(13,14)15-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3

Standard InChI Key:  MZVIAOIHWLOXPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    1.1042   -3.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -3.8625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -3.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -5.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -3.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -4.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -3.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8  3  2  0
  9  2  2  0
 10  4  2  0
 11  4  2  0
 12  4  1  0
 13  6  2  0
 14  7  2  0
 15 14  1  0
 16 13  1  0
  6  7  1  0
 16 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA142025

   2-Methylsulfonyloxyisoindole-1,3-dione

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: 241.22

Molecular Weight (Monoisotopic): 241.0045

AlogP: 0.17

#Rotatable Bonds: 2

Polar Surface Area: 80.75

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.33

CX LogD: 0.33

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.69

Np Likeness Score: -0.50

References

1. Kerrigan JE, Shirley JJ.  (1996)  2-[(Alkylsulfonyl)oxy]-6-substituted-1H-isoindole-1,3(2H)-dione mechanism-based inhibitors of human leukocyte elastase,  6  (4): [10.1016/0960-894X(96)00038-8]

2. Chan CL, Lien EJ, Tokes ZA..  (1987)  Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of 2-hydroxy-1H-isoindolediones as new cytostatic agents.,  30  (3): [PMID:3820223] [10.1021/jm00386a012]

3. Parsons WH, Rutland NT, Crainic JA, Cardozo JM, Chow AS, Andrews CL, Sheehan BK..  (2021)  Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL.,  49  [PMID:34311087] [10.1016/j.bmcl.2021.128290]

Source

Source(1):

• Scientific Literature