Methanesulfonic acid 5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

ID: ALA101966

PubChem CID: 364533

Max Phase: Preclinical

Molecular Formula: C9H8N2O5S

Molecular Weight: 256.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)ON1C(=O)c2ccc(N)cc2C1=O

Standard InChI:  InChI=1S/C9H8N2O5S/c1-17(14,15)16-11-8(12)6-3-2-5(10)4-7(6)9(11)13/h2-4H,10H2,1H3

Standard InChI Key:  BNULMKWKKIYHKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.3167   -0.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.5625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -0.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    0.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -2.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  7  1  0
  6  3  1  0
  7  1  1  0
  8  6  2  0
  9  2  2  0
 10  3  2  0
 11  5  2  0
 12  5  2  0
 13  4  2  0
 14 13  1  0
 15  5  1  0
 16  8  1  0
 17 14  1  0
  6  4  1  0
 16 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA101966

   5-Amino-2-((methylsulfonyl)oxy)-1H-isoindole-1,3(2H)-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: 256.24

Molecular Weight (Monoisotopic): 256.0154

AlogP: -0.24

#Rotatable Bonds: 2

Polar Surface Area: 106.77

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.55

CX LogP: -0.50

CX LogD: -0.50

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.58

Np Likeness Score: -0.50

References

1. Kerrigan JE, Walters MC, Forrester KJ, Crowder JB, Christopher LJ..  (2000)  6-Acylamino-2-[(alkylsulfonyl)oxy]-1H-isoindole-1,3-dione mechanism-based inhibitors of human leukocyte elastase.,  10  (1): [PMID:10636236] [10.1016/s0960-894x(99)00588-0]

2. 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]

3. 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]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays