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

ID: ALA271126

PubChem CID: 44457088

Max Phase: Preclinical

Molecular Formula: C21H15F3N2O3

Molecular Weight: 400.36

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C(=O)O)c(Nc2cccc(C(F)(F)F)c2)c1)c1ccccc1

Standard InChI:  InChI=1S/C21H15F3N2O3/c22-21(23,24)14-7-4-8-15(11-14)25-18-12-16(9-10-17(18)20(28)29)26-19(27)13-5-2-1-3-6-13/h1-12,25H,(H,26,27)(H,28,29)

Standard InChI Key:  SDHGFCAZMDTMEG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.5609  -16.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461  -16.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297  -16.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325  -15.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479  -15.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196  -15.1853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036  -15.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038  -16.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4309  -15.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417  -14.7458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494  -15.8763    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121  -14.4545    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8508  -14.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5665  -13.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463  -17.6694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319  -18.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321  -18.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4174  -17.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8471  -19.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477  -20.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328  -20.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158  -20.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188  -19.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  5  7  1  0
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  3  4  2  0
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  8  9  2  0
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 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
 11 12  1  0
 23 25  2  0
  6  1  1  0
 25 26  1  0
 12 13  2  0
 26 27  2  0
 13  8  1  0
 27 28  1  0
  1  2  2  0
 28 29  2  0
 29 23  1  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: 400.36Molecular Weight (Monoisotopic): 400.1035AlogP: 5.40#Rotatable Bonds: 5
Polar Surface Area: 78.43Molecular Species: ACIDHBA: 3HBD: 3
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.94CX Basic pKa: CX LogP: 6.34CX LogD: 3.15
Aromatic Rings: 3Heavy Atoms: 29QED Weighted: 0.54Np Likeness Score: -1.33

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