(2RS,3RS)-2-(4-Chlorophenyl)-N-(2-hydroxyethyl)-5-oxo-1-(4-sulfamoylphenyl)pyrrolidine-3-carboxamide

ID: ALA4476050

PubChem CID: 155538083

Max Phase: Preclinical

Molecular Formula: C19H20ClN3O5S

Molecular Weight: 437.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(N2C(=O)C[C@H](C(=O)NCCO)[C@H]2c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C19H20ClN3O5S/c20-13-3-1-12(2-4-13)18-16(19(26)22-9-10-24)11-17(25)23(18)14-5-7-15(8-6-14)29(21,27)28/h1-8,16,18,24H,9-11H2,(H,22,26)(H2,21,27,28)/t16-,18+/m0/s1

Standard InChI Key:  ZTNPVYBROJICQU-FUHWJXTLSA-N

Molfile:  

 
     RDKit          2D

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    4.3666  -13.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838  -13.0049    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7752  -12.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7834  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6006  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550  -16.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1920  -16.2737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333  -16.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1908  -15.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995  -15.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986  -14.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1898  -13.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803  -14.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4847  -15.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218  -16.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666  -18.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495  -18.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7682  -18.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5582  -16.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256  -15.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150  -15.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4015  -15.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031  -16.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143  -16.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940  -12.5950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938  -15.1104    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5853  -18.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869  -19.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8041  -19.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7  9  1  0
  8 15  1  1
  4 16  1  6
 16 17  2  0
 16 18  1  0
  6 19  2  0
 15 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 15  1  0
 12  2  1  0
  2 25  1  0
 22 26  1  0
 18 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476050

   ---

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: 437.91

Molecular Weight (Monoisotopic): 437.0812

AlogP: 1.19

#Rotatable Bonds: 6

Polar Surface Area: 129.80

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 0.40

CX LogD: 0.40

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -1.11

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