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

ID: ALA554968

PubChem CID: 45267468

Max Phase: Preclinical

Molecular Formula: C13H15FN2O4

Molecular Weight: 282.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15FN2O4/c1-6(2)12(18)16-10-4-8(13(19)20)9(14)5-11(10)15-7(3)17/h4-6H,1-3H3,(H,15,17)(H,16,18)(H,19,20)

Standard InChI Key:  VQVLXOSWRPZJMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.0103   -4.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -5.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -6.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -5.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -4.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -4.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -3.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -3.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -3.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248   -4.5354    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -7.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -7.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -8.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248   -7.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8669   -6.1854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1524   -5.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620   -6.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1524   -4.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8669   -4.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620   -4.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  2  3  1  0
  3 11  1  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  2  0
 16 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA554968

   4-Acetamido-2-fluoro-5-(2-methylpropanoylamino)benzoic 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: 282.27

Molecular Weight (Monoisotopic): 282.1016

AlogP: 2.08

#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: 1.49

CX LogD: -1.94

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: -1.16

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