4-{[(5-Benzyl-4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)sulfanyl]acetyl}-2-chlorobenzenesulfonamide

ID: ALA2443196

PubChem CID: 136259430

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O4S2

Molecular Weight: 463.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(SCC(=O)c2ccc(S(N)(=O)=O)c(Cl)c2)[nH]c(=O)c1Cc1ccccc1

Standard InChI:  InChI=1S/C20H18ClN3O4S2/c1-12-15(9-13-5-3-2-4-6-13)19(26)24-20(23-12)29-11-17(25)14-7-8-18(16(21)10-14)30(22,27)28/h2-8,10H,9,11H2,1H3,(H2,22,27,28)(H,23,24,26)

Standard InChI Key:  CWKSXTMMSXHYOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   11.4154   -8.5554    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0023   -9.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8272   -9.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1313   -7.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1301   -8.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8449   -8.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5613   -8.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5584   -7.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8431   -6.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2714   -6.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9873   -7.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2682   -6.0725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7002   -6.8921    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.4162   -7.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4162   -8.1257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1313   -8.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8452   -8.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8394   -7.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1237   -6.8850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7012   -8.1425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8447   -9.3814    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.5507   -6.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5617   -8.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1340   -9.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2741   -8.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9894   -8.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7013   -8.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6975   -7.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9760   -6.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2671   -7.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 14  1  0
  5  1  1  0
  1 20  1  0
  6 21  1  0
 18 22  2  0
 17 23  1  0
 16 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2443196

   ---

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: 463.97

Molecular Weight (Monoisotopic): 463.0427

AlogP: 2.94

#Rotatable Bonds: 7

Polar Surface Area: 122.98

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.75

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.32

Np Likeness Score: -1.88

References

1. Čapkauskaitė E, Zubrienė A, Smirnov A, Torresan J, Kišonaitė M, Kazokaitė J, Gylytė J, Michailovienė V, Jogaitė V, Manakova E, Gražulis S, Tumkevičius S, Matulis D..  (2013)  Benzenesulfonamides with pyrimidine moiety as inhibitors of human carbonic anhydrases I, II, VI, VII, XII, and XIII.,  21  (22): [PMID:24103428] [10.1016/j.bmc.2013.09.029]

Source

Source(1):

• Scientific Literature