4-Acetamido-5-(2-methylbutanamido)-2-fluoro benzoic acid

ID: ALA560987

PubChem CID: 45269200

Max Phase: Preclinical

Molecular Formula: C14H17FN2O4

Molecular Weight: 296.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H17FN2O4/c1-4-7(2)13(19)17-11-5-9(14(20)21)10(15)6-12(11)16-8(3)18/h5-7H,4H2,1-3H3,(H,16,18)(H,17,19)(H,20,21)

Standard InChI Key:  TVKITEIFJSVNMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    4.8470  -11.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615  -12.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759  -11.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759  -11.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615  -10.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8470  -11.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325  -10.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180  -11.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325   -9.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325  -12.3325    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9904  -12.3325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9904  -13.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7049  -13.5700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759  -13.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9904  -10.6825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7049  -11.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7049  -11.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193  -10.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1338  -11.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1338  -11.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193   -9.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1 10  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA560987

   4-Acetamido-2-fluoro-5-(2-methylbutanoylamino)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: 296.30

Molecular Weight (Monoisotopic): 296.1172

AlogP: 2.47

#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: 1.94

CX LogD: -1.50

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.78

Np Likeness Score: -0.94

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