Methyl (2RS,3RS)-5-oxo-2-phenyl-1-(4-sulfamoylphenyl)pyrrolidine-3-carboxylate

ID: ALA4482951

PubChem CID: 155539868

Max Phase: Preclinical

Molecular Formula: C18H18N2O5S

Molecular Weight: 374.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H]1CC(=O)N(c2ccc(S(N)(=O)=O)cc2)[C@H]1c1ccccc1

Standard InChI:  InChI=1S/C18H18N2O5S/c1-25-18(22)15-11-16(21)20(17(15)12-5-3-2-4-6-12)13-7-9-14(10-8-13)26(19,23)24/h2-10,15,17H,11H2,1H3,(H2,19,23,24)/t15-,17+/m1/s1

Standard InChI Key:  GZJKGWRWCBDNPT-WBVHZDCISA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   19.6725   -7.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7458   -4.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1680   -4.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7447   -4.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7417   -7.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4532   -3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4377   -6.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1496   -7.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4535   -5.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8568   -7.7455    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2606   -7.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8605   -8.5635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1708   -4.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7406   -6.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4439   -7.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1446   -6.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0360   -6.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0375   -5.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2550   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7688   -5.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2526   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8415   -4.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2492   -3.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0243   -4.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8397   -2.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9994   -7.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5 15  1  0
 15  8  2  0
  6  2  2  0
 16  7  2  0
  2  4  1  0
 10 12  1  0
  8 16  1  0
 17 14  1  0
  8 10  1  0
  9  3  1  0
  7 14  1  0
 10 11  2  0
 18  4  1  6
  1 10  2  0
 13  6  1  0
 14  5  2  0
  3 13  2  0
  4  9  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 19 22  1  1
 22 23  1  0
 22 24  2  0
 23 25  1  0
 21 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4482951

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.42

Molecular Weight (Monoisotopic): 374.0936

AlogP: 1.60

#Rotatable Bonds: 4

Polar Surface Area: 106.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: 1.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -0.73

References

1. Kalinin S, Nocentini A, Kovalenko A, Sharoyko V, Bonardi A, Angeli A, Gratteri P, Tennikova TB, Supuran CT, Krasavin M..  (2019)  From random to rational: A discovery approach to selective subnanomolar inhibitors of human carbonic anhydrase IV based on the Castagnoli-Cushman multicomponent reaction.,  182  [PMID:31476557] [10.1016/j.ejmech.2019.111642]

Source

Source(1):

• Scientific Literature