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4-acetamido-2-[(3-trifluoromethylphenyl)amino]benzoic acid

ID: ALA429437

PubChem CID: 25099135

Max Phase: Preclinical

Molecular Formula: C16H13F3N2O3

Molecular Weight: 338.29

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(C(=O)O)c(Nc2cccc(C(F)(F)F)c2)c1

Standard InChI:  InChI=1S/C16H13F3N2O3/c1-9(22)20-12-5-6-13(15(23)24)14(8-12)21-11-4-2-3-10(7-11)16(17,18)19/h2-8,21H,1H3,(H,20,22)(H,23,24)

Standard InChI Key:  NCXZIMSKJCYJMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   11.7027   -8.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7016   -9.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4164  -10.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1328   -9.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1300   -8.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4146   -8.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8429   -8.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5589   -8.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5587   -9.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2738   -9.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9877   -9.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9820   -8.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2662   -8.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6934   -8.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4042   -7.9083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.1119   -9.0388    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2746   -7.6170    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4117   -7.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1249   -7.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6960   -7.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4162  -10.8319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1306  -11.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1304  -12.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8451  -10.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
 13  8  1  0
  1  2  2  0
 12 14  1  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 14 16  1  0
  7  8  1  0
 14 17  1  0
  8  9  2  0
  4  5  1  0
 18 19  1  0
 18 20  2  0
  6 18  1  0
  9 10  1  0
  3 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  2  0
 22 23  1  0
  5  6  2  0
 22 24  2  0
M  END

Alternative Forms

Associated Targets(Human)

MPO Tchem Myeloperoxidase (1002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 338.29Molecular Weight (Monoisotopic): 338.0878AlogP: 4.11#Rotatable Bonds: 4
Polar Surface Area: 78.43Molecular Species: ACIDHBA: 3HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 3.95CX Basic pKa: CX LogP: 4.49CX LogD: 1.30
Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.78Np Likeness Score: -1.35

References

1. Van Antwerpen P, Prévost M, Zouaoui-Boudjeltia K, Babar S, Legssyer I, Moreau P, Moguilevsky N, Vanhaeverbeek M, Ducobu J, Nève J, Dufrasne F..  (2008)  Conception of myeloperoxidase inhibitors derived from flufenamic acid by computational docking and structure modification.,  16  (4): [PMID:18063373] [10.1016/j.bmc.2007.11.025]
2. Tidén, Anna-Karin AK and 16 more authors.  2011-10-28  2-thioxanthines are mechanism-based inactivators of myeloperoxidase that block oxidative stress during inflammation.  [PMID:21880720]
3. Roth, Aaron and 9 more authors.  2014-11-15  Inhibition of myeloperoxidase: evaluation of 2H-indazoles and 1H-indazolones.  [PMID:25438766]

Source