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

ID: ALA2443203

PubChem CID: 72696858

Max Phase: Preclinical

Molecular Formula: C15H15N3O6S2

Molecular Weight: 397.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc(SCC(=O)c2cccc(S(N)(=O)=O)c2)[nH]c1=O

Standard InChI:  InChI=1S/C15H15N3O6S2/c1-2-24-14(21)11-7-17-15(18-13(11)20)25-8-12(19)9-4-3-5-10(6-9)26(16,22)23/h3-7H,2,8H2,1H3,(H2,16,22,23)(H,17,18,20)

Standard InChI Key:  WVFQNCZNCJDNCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    6.3659  -12.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409  -12.4268    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534  -13.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311  -10.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300  -11.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5447  -11.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612  -11.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583  -10.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5430   -9.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9712   -9.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6872  -10.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9681   -9.1206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4000   -9.9402    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1161  -10.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1161  -11.1739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8312  -11.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5450  -11.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5393  -10.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8235   -9.9331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300  -12.8419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2507   -9.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2615  -11.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9739  -11.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2657  -12.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6904  -11.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4028  -11.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  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
  6  2  1  0
  2 20  1  0
 18 21  2  0
 17 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2443203

   ethyl 6-oxo-2-[2-oxo-2-(3-sulfamoylphenyl)ethyl]sulfanyl-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: 397.43

Molecular Weight (Monoisotopic): 397.0402

AlogP: 0.57

#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: 7.38

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.30

Np Likeness Score: -2.05

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