Ethyl 2-({2-[4-(aminosulfonyl)-3-chlorophenyl]-2-oxoethyl}sulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

ID: ALA2443202

PubChem CID: 72696724

Max Phase: Preclinical

Molecular Formula: C15H14ClN3O6S2

Molecular Weight: 431.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc(SCC(=O)c2ccc(S(N)(=O)=O)c(Cl)c2)[nH]c1=O

Standard InChI:  InChI=1S/C15H14ClN3O6S2/c1-2-25-14(22)9-6-18-15(19-13(9)21)26-7-11(20)8-3-4-12(10(16)5-8)27(17,23)24/h3-6H,2,7H2,1H3,(H2,17,23,24)(H,18,19,21)

Standard InChI Key:  LCFYOXFUBTVVRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    2.7119  -12.1375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988  -12.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236  -12.8523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276  -10.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265  -11.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1415  -12.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577  -11.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549  -10.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396  -10.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678  -10.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2838  -10.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -9.6545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9967  -10.4741    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7126  -10.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7126  -11.7077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4278  -12.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1416  -11.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1359  -10.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4201  -10.4670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976  -11.7245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412  -12.9634    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8473  -10.4553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8582  -12.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8624  -12.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5704  -11.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2871  -12.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9994  -11.6875    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
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2443202

   ethyl 2-[2-(3-chloro-4-sulfamoylphenyl)-2-oxoethyl]sulfanyl-6-oxo-1H-pyrimidine-5-carboxylate

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: 431.88

Molecular Weight (Monoisotopic): 431.0013

AlogP: 1.22

#Rotatable Bonds: 7

Polar Surface Area: 149.28

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.51

CX Basic pKa: ┄

CX LogP: 1.32

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -2.06

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