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

ID: ALA541257

PubChem CID: 45273487

Max Phase: Preclinical

Molecular Formula: C15H17FN2O4

Molecular Weight: 308.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(F)c(C(=O)O)cc1NC(=O)C1CCCC1

Standard InChI:  InChI=1S/C15H17FN2O4/c1-8(19)17-13-7-11(16)10(15(21)22)6-12(13)18-14(20)9-4-2-3-5-9/h6-7,9H,2-5H2,1H3,(H,17,19)(H,18,20)(H,21,22)

Standard InChI Key:  ZWVFCXAGLPMNES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    7.2426    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    0.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9570    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9570    2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715    3.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3860    2.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    3.4505    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    0.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    0.1505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9570   -0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715    0.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9570   -1.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6245   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3695   -2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5445   -2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2896   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 18 19  1  0
  7  9  2  0
  4  5  1  0
  1 10  1  0
  2  3  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA541257

   4-Acetamido-5-(cyclopentanecarbonylamino)-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: 308.31

Molecular Weight (Monoisotopic): 308.1172

AlogP: 2.61

#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: 1.92

CX LogD: -1.52

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: -1.38

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