5-Acetyl-N-(4-amino-2-(methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)-2-methoxybenzenesulfonamide

ID: ALA4537016

PubChem CID: 155548762

Max Phase: Preclinical

Molecular Formula: C14H16N4O5S2

Molecular Weight: 384.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C(C)=O)cc1S(=O)(=O)Nc1c(N)nc(SC)[nH]c1=O

Standard InChI:  InChI=1S/C14H16N4O5S2/c1-7(19)8-4-5-9(23-2)10(6-8)25(21,22)18-11-12(15)16-14(24-3)17-13(11)20/h4-6,18H,1-3H3,(H3,15,16,17,20)

Standard InChI Key:  CXNHYQKFKGEQGE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   16.6121   -4.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3220   -3.8301    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6168   -3.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5478   -1.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7324   -1.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3255   -2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7329   -3.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5514   -3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9546   -2.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7718   -2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1825   -3.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1783   -1.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5083   -2.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0999   -1.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7277   -4.5394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3163   -5.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5019   -5.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0906   -5.9421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4964   -6.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3178   -6.6531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0987   -4.5261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0859   -7.3590    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2687   -7.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5427   -5.9456    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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6 13  1  0
 13 14  1  0
  7  2  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 16  1  0
 17 22  1  0
 19 23  1  0
 23 24  1  0
 21 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537016

   ---

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: 384.44

Molecular Weight (Monoisotopic): 384.0562

AlogP: 1.09

#Rotatable Bonds: 6

Polar Surface Area: 144.24

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.34

CX Basic pKa: ┄

CX LogP: 0.31

CX LogD: 0.02

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.38

Np Likeness Score: -1.69

References

1. Castaño LF, Cuartas V, Bernal A, Insuasty A, Guzman J, Vidal O, Rubio V, Puerto G, Lukáč P, Vimberg V, Balíková-Novtoná G, Vannucci L, Janata J, Quiroga J, Abonia R, Nogueras M, Cobo J, Insuasty B..  (2019)  New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity.,  176  [PMID:31096118] [10.1016/j.ejmech.2019.05.013]

Source

Source(1):

• Scientific Literature