3-{[(5-Butylpyrimidin-2-yl)sulfanyl]acetyl}benzenesulfonamide

ID: ALA2443193

PubChem CID: 72697000

Max Phase: Preclinical

Molecular Formula: C16H19N3O3S2

Molecular Weight: 365.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1cnc(SCC(=O)c2cccc(S(N)(=O)=O)c2)nc1

Standard InChI:  InChI=1S/C16H19N3O3S2/c1-2-3-5-12-9-18-16(19-10-12)23-11-15(20)13-6-4-7-14(8-13)24(17,21)22/h4,6-10H,2-3,5,11H2,1H3,(H2,17,21,22)

Standard InChI Key:  HIYNXKSGYONSGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.4499  -23.4830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249  -23.4830    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374  -24.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151  -21.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140  -22.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288  -22.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453  -22.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424  -21.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271  -21.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553  -21.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7713  -21.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522  -20.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4842  -20.9963    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2002  -21.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2002  -22.2298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9154  -22.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292  -22.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6235  -21.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9077  -20.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140  -23.8980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3458  -22.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0581  -22.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7747  -22.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4870  -22.2097    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  2  0
 19 14  1  0
  6  2  1  0
  2 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2443193

   3-[2-(5-Butylpyrimidin-2-yl)sulfanylacetyl]benzenesulfonamide

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: 365.48

Molecular Weight (Monoisotopic): 365.0868

AlogP: 2.44

#Rotatable Bonds: 8

Polar Surface Area: 103.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 1.49

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: -1.74

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