1,3-dioxo-2-(4-sulfamoylbenzamido)isoindoline-5-carboxylic acid

ID: ALA5205140

PubChem CID: 168295333

Max Phase: Preclinical

Molecular Formula: C16H11N3O7S

Molecular Weight: 389.35

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(C(=O)NN2C(=O)c3ccc(C(=O)O)cc3C2=O)cc1

Standard InChI:  InChI=1S/C16H11N3O7S/c17-27(25,26)10-4-1-8(2-5-10)13(20)18-19-14(21)11-6-3-9(16(23)24)7-12(11)15(19)22/h1-7H,(H,18,20)(H,23,24)(H2,17,25,26)

Standard InChI Key:  CHTDZQLORQKFFG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -3.2588    0.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322    0.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -0.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424   -0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -0.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475    0.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -0.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339    1.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -1.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -0.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    0.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    0.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.3365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486    0.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395   -0.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9147   -0.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738    0.6208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    1.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6880    0.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733    0.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733    1.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880    0.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  1  0
  9  7  1  0
  8 10  2  0
  7 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 14 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  2  0
 21 24  2  0
 25  1  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5205140

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 389.35

Molecular Weight (Monoisotopic): 389.0318

AlogP: -0.03

#Rotatable Bonds: 4

Polar Surface Area: 163.94

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.51

CX Basic pKa: ┄

CX LogP: 0.22

CX LogD: -3.19

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -1.17

References

1. Kumar S, Rulhania S, Jaswal S, Monga V..  (2021)  Recent advances in the medicinal chemistry of carbonic anhydrase inhibitors.,  209  [PMID:33121862] [10.1016/j.ejmech.2020.112923]

Source

Source(1):

• Scientific Literature