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

ID: ALA550657

PubChem CID: 45270881

Max Phase: Preclinical

Molecular Formula: C16H19FN2O4

Molecular Weight: 322.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(F)c(C(=O)O)cc1NC(=O)C1CCCCC1

Standard InChI:  InChI=1S/C16H19FN2O4/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/h7-8,10H,2-6H2,1H3,(H,18,20)(H,19,21)(H,22,23)

Standard InChI Key:  QYPSVNXZUYHQOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.2579    1.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869    1.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724    1.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724    2.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579    3.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869    3.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    1.8400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -0.6350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4013   -0.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -1.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4013    0.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1158    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1158    1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592   -0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303   -0.6350    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  1  0
  4  5  1  0
 19 20  1  0
  1 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
  3 11  1  0
 22 23  1  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA550657

   4-Acetamido-5-(cyclohexanecarbonylamino)-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: 322.34

Molecular Weight (Monoisotopic): 322.1329

AlogP: 3.00

#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: 2.36

CX LogD: -1.07

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -1.33

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