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

ID: ALA143544

PubChem CID: 44360733

Max Phase: Preclinical

Molecular Formula: C11H12N2O5S

Molecular Weight: 284.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)S(=O)(=O)ON1C(=O)c2ccc(N)cc2C1=O

Standard InChI:  InChI=1S/C11H12N2O5S/c1-6(2)19(16,17)18-13-10(14)8-4-3-7(12)5-9(8)11(13)15/h3-6H,12H2,1-2H3

Standard InChI Key:  QXEHCZJISUTFLD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  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
    2.7542   -3.8625    0.0000 S   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
    0.6250   -4.5417    0.0000 C   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   -3.4625    0.0000 C   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
    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
   -0.8875   -4.7042    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
   -0.8875   -3.0500    0.0000 C   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
   -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
   -2.3125   -3.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  1  1  0
  5  1  1  0
  6  3  1  0
  7  4  1  0
  8  2  2  0
  9  2  2  0
 10  7  2  0
 11  3  2  0
 12  4  2  0
 13  6  2  0
 14  2  1  0
 15 13  1  0
 16 10  1  0
 17 15  1  0
 18 14  1  0
 19 14  1  0
  7  6  1  0
 16 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA143544

   (5-Amino-1,3-dioxoisoindol-2-yl) propane-2-sulfonate

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: 284.29

Molecular Weight (Monoisotopic): 284.0467

AlogP: 0.53

#Rotatable Bonds: 3

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: 1.62

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.64

Np Likeness Score: -0.44

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]

Source

Source(1):

• Scientific Literature