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

ID: ALA571446

PubChem CID: 45271722

Max Phase: Preclinical

Molecular Formula: C13H13FN2O4

Molecular Weight: 280.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(F)c(C(=O)O)cc1NC(=O)C1CC1

Standard InChI:  InChI=1S/C13H13FN2O4/c1-6(17)15-11-5-9(14)8(13(19)20)4-10(11)16-12(18)7-2-3-7/h4-5,7H,2-3H2,1H3,(H,15,17)(H,16,18)(H,19,20)

Standard InChI Key:  LJEAVQYWGNGCQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -1.8997   -1.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -2.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1853   -2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1853   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -1.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2437   -1.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.1772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.1772    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3287   -2.6522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431   -2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7576   -2.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -3.4772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1853   -3.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -3.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1853   -4.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5978   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -5.4292    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
 19 18  1  0
 20 19  1  0
 18 20  1  0
  7  9  2  0
  4  5  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA571446

   4-Acetamido-5-(cyclopropanecarbonylamino)-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: 280.26

Molecular Weight (Monoisotopic): 280.0859

AlogP: 1.83

#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: 1.03

CX LogD: -2.41

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: -1.49

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