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

ID: ALA558122

PubChem CID: 45273498

Max Phase: Preclinical

Molecular Formula: C13H15FN2O4

Molecular Weight: 282.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15FN2O4/c1-3-4-12(18)16-10-5-8(13(19)20)9(14)6-11(10)15-7(2)17/h5-6H,3-4H2,1-2H3,(H,15,17)(H,16,18)(H,19,20)

Standard InChI Key:  FSNZWXMHZZAIPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -0.6437   -2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -3.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852   -2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727   -1.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582   -0.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582   -3.2219    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -3.2219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -4.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2141   -4.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852   -4.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -1.5719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2141   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2141   -2.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431   -2.8094    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
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA558122

   4-Acetamido-5-(butanoylamino)-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: 282.27

Molecular Weight (Monoisotopic): 282.1016

AlogP: 2.22

#Rotatable Bonds: 5

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: 1.39

CX LogD: -2.04

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.77

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