3-(5-methyl-2-oxoindolin-3-ylideneamino)benzenesulfonamide

ID: ALA3633555

PubChem CID: 137028519

Max Phase: Preclinical

Molecular Formula: C15H13N3O3S

Molecular Weight: 315.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)/C(=N/c1cccc(S(N)(=O)=O)c1)C(=O)N2

Standard InChI:  InChI=1S/C15H13N3O3S/c1-9-5-6-13-12(7-9)14(15(19)18-13)17-10-3-2-4-11(8-10)22(16,20)21/h2-8H,1H3,(H2,16,20,21)(H,17,18,19)

Standard InChI Key:  MGEFUUBEKQFGOS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.2779   -6.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0736   -6.0771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2493   -6.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -4.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5991   -4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944   -3.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201   -2.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -1.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4535   -7.2154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 11 13  2  0
  6 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18  2  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3633555

   ---

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: 315.35

Molecular Weight (Monoisotopic): 315.0678

AlogP: 1.72

#Rotatable Bonds: 2

Polar Surface Area: 101.62

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.78

CX Basic pKa: ┄

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: -1.50

References

1. Ibrahim HS, Abou-Seri SM, Tanc M, Elaasser MM, Abdel-Aziz HA, Supuran CT..  (2015)  Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII.,  103  [PMID:26408817] [10.1016/j.ejmech.2015.09.021]

2. Akdemir A, Güzel-Akdemir Ö, Karalı N, Supuran CT..  (2016)  Isatin analogs as novel inhibitors of Candida spp. β-carbonic anhydrase enzymes.,  24  (8): [PMID:26951893] [10.1016/j.bmc.2016.02.036]

Source

Source(1):

• Scientific Literature