Toluene-4-sulfonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

ID: ALA142827

Cas Number: 56530-39-3

PubChem CID: 2173330

Max Phase: Preclinical

Molecular Formula: C15H11NO5S

Molecular Weight: 317.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)ON2C(=O)c3ccccc3C2=O)cc1

Standard InChI:  InChI=1S/C15H11NO5S/c1-10-6-8-11(9-7-10)22(19,20)21-16-14(17)12-4-2-3-5-13(12)15(16)18/h2-9H,1H3

Standard InChI Key:  MMZCYVBYIOUFEO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  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   -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
    3.5792   -3.8625    0.0000 C   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
    2.7542   -3.0375    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
    0.8667   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -3.8625    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
   -0.8875   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -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  5  1  0
  3  1  1  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8  2  1  0
  9  2  2  0
 10  2  2  0
 11  4  2  0
 12  3  2  0
 13  8  2  0
 14  8  1  0
 15 14  2  0
 16 13  1  0
 17 15  1  0
 18  7  2  0
 19  6  2  0
 20 17  1  0
 21 18  1  0
 22 19  1  0
  6  7  1  0
 22 21  2  0
 17 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA142827

   (1,3-Dioxoisoindol-2-yl) 4-methylbenzenesulfonate

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: 317.32

Molecular Weight (Monoisotopic): 317.0358

AlogP: 1.91

#Rotatable Bonds: 3

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: 2.96

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -0.72

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. Nandhikonda P, Lynt WZ, McCallum MM, Ara T, Baranowski AM, Yuan NY, Pearson D, Bikle DD, Guy RK, Arnold LA..  (2012)  Discovery of the first irreversible small molecule inhibitors of the interaction between the vitamin D receptor and coactivators.,  55  (10): [PMID:22563729] [10.1021/jm300460c]

Source

Source(1):

• Scientific Literature