4-nitro-N-(4-sulfamoylphenylcarbamothioyl)benzamide

ID: ALA2298035

PubChem CID: 3476048

Max Phase: Preclinical

Molecular Formula: C14H12N4O5S2

Molecular Weight: 380.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(NC(=S)NC(=O)c2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C14H12N4O5S2/c15-25(22,23)12-7-3-10(4-8-12)16-14(24)17-13(19)9-1-5-11(6-2-9)18(20)21/h1-8H,(H2,15,22,23)(H2,16,17,19,24)

Standard InChI Key:  VTQFCLNJYSQGAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   32.0506   -3.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0495   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7575   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4672   -4.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4644   -3.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7558   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1705   -3.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8798   -3.6808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1675   -2.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5859   -3.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2952   -3.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5829   -2.4523    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.0014   -3.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7066   -3.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4123   -3.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4096   -2.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6954   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9927   -2.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1153   -2.0310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.8250   -2.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7010   -1.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5182   -1.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3396   -4.9210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3389   -5.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6322   -4.5119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 23 24  2  0
 23 25  1  0
  2 23  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2298035

   4-nitro-N-[(4-sulfamoylphenyl)carbamothioyl]benzamide

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: 380.41

Molecular Weight (Monoisotopic): 380.0249

AlogP: 1.37

#Rotatable Bonds: 4

Polar Surface Area: 144.43

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 2.15

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: -2.27

References

1. Saeed A, Zaib S, Pervez A, Mumtaz A, Shahid M, Iqbal J.  (2013)  Synthesis, molecular docking studies, and in vitro screening of sulfanilamide-thiourea hybrids as antimicrobial and urease inhibitors,  22  (8): [10.1007/s00044-012-0376-4]

2. Mahdavi M, Shirazi MS, Taherkhani R, Saeedi M, Alipour E, Moghadam FH, Moradi A, Nadri H, Emami S, Firoozpour L, Shafiee A, Foroumadi A..  (2014)  Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors.,  82  [PMID:24927051] [10.1016/j.ejmech.2014.05.054]

3. Liu L, Wang W, Huang J, Zhao Z, Li H, Xu Y..  (2018)  Novel benzoyl thioureido benzene sulfonamides as highly potent and selective inhibitors of carbonic anhydrase IX: optimization and bioactive studies.,  9  (12): [PMID:30746068] [10.1039/C8MD00392K]

Source

Source(1):

• Scientific Literature