4-Acetamido-5-benzamido-2-fluoro benzoic acid

ID: ALA552203

PubChem CID: 45270059

Max Phase: Preclinical

Molecular Formula: C16H13FN2O4

Molecular Weight: 316.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(F)c(C(=O)O)cc1NC(=O)c1ccccc1

Standard InChI:  InChI=1S/C16H13FN2O4/c1-9(20)18-14-8-12(17)11(16(22)23)7-13(14)19-15(21)10-5-3-2-4-6-10/h2-8H,1H3,(H,18,20)(H,19,21)(H,22,23)

Standard InChI Key:  ZQDKVKXSUSRCJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -1.1059    1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230    0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230    1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914    1.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914    2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    3.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230    3.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    1.8243    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914   -0.6507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375    0.1743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    1.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809    0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954   -0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664   -0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 12 14  1  0
  6  7  1  0
  4 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
 16 18  2  0
  7  9  2  0
 17 19  2  0
  4  5  1  0
 19 20  1  0
  1 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  3 11  1  0
 22 23  2  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA552203

   4-Acetamido-5-benzamido-2-fluorobenzoic acid

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: 316.29

Molecular Weight (Monoisotopic): 316.0859

AlogP: 2.73

#Rotatable Bonds: 4

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.25

CX Basic pKa: ┄

CX LogP: 2.10

CX LogD: -1.33

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: -1.24

References

1. Magesh S, Savita V, Moriya S, Suzuki T, Miyagi T, Ishida H, Kiso M..  (2009)  Human sialidase inhibitors: design, synthesis, and biological evaluation of 4-acetamido-5-acylamido-2-fluoro benzoic acids.,  17  (13): [PMID:19450982] [10.1016/j.bmc.2009.04.065]

Source

Source(1):

• Scientific Literature