N-(4-Fluoro-3-nitrophenyl)-2,4-dihydroxythiobenzamide

ID: ALA2269788

PubChem CID: 136244978

Max Phase: Preclinical

Molecular Formula: C13H9FN2O4S

Molecular Weight: 308.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(NC(=S)c2ccc(O)cc2O)ccc1F

Standard InChI:  InChI=1S/C13H9FN2O4S/c14-10-4-1-7(5-11(10)16(19)20)15-13(21)9-3-2-8(17)6-12(9)18/h1-6,17-18H,(H,15,21)

Standard InChI Key:  VGXPHMSXASNFQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   18.6867   -3.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6855   -4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3936   -5.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1032   -4.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1004   -3.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3918   -3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8116   -5.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775   -5.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8066   -3.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5158   -3.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8035   -2.7053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.2220   -3.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9296   -3.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6353   -3.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6327   -2.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9185   -2.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2157   -2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3383   -2.2856    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.3470   -3.9223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0533   -3.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3497   -4.7395    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
  4  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 19 20  2  0
 19 21  1  0
 14 19  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2269788

   ---

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: 308.29

Molecular Weight (Monoisotopic): 308.0267

AlogP: 2.93

#Rotatable Bonds: 3

Polar Surface Area: 95.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.42

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.39

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: -1.27

References

1. Niewiadomy A, Matysiak J, Fekner Z, Czeczko R.  (2006)  Synthesis, antifungal activity and SAR of N-substituted and N,N-disubstituted 2,4-dihydroxythiobenzamides,  31  (1): [10.1584/jpestics.31.14]

Source

Source(1):

• Scientific Literature