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(2E)-4-[(3-carboxy-1-oxopropenyl)amino]-2-[(3-trifluoromethylphenyl)amino]benzoic acid

ID: ALA270911

PubChem CID: 44457087

Max Phase: Preclinical

Molecular Formula: C18H13F3N2O5

Molecular Weight: 394.31

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13F3N2O5/c19-18(20,21)10-2-1-3-11(8-10)22-14-9-12(4-5-13(14)17(27)28)23-15(24)6-7-16(25)26/h1-9,22H,(H,23,24)(H,25,26)(H,27,28)/b7-6+

Standard InChI Key:  RDLWYLITKWMZLV-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

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    2.7766  -16.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914  -16.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078  -16.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050  -15.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896  -15.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9179  -15.3270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6339  -15.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6337  -16.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3488  -16.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0627  -16.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0570  -15.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3412  -15.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7684  -15.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792  -14.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1869  -16.0179    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.3496  -14.5961    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867  -14.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999  -14.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710  -14.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912  -17.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056  -18.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2054  -19.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201  -17.8114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908  -19.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906  -20.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764  -20.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2054  -20.7014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
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  5  6  2  0
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 11 12  1  0
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  6  1  1  0
 25 26  1  0
 12 13  2  0
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 26 27  1  0
 26 28  2  0
M  END

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: 394.31Molecular Weight (Monoisotopic): 394.0777AlogP: 3.73#Rotatable Bonds: 6
Polar Surface Area: 115.73Molecular Species: ACIDHBA: 4HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 2.88CX Basic pKa: CX LogP: 4.67CX LogD: -2.01
Aromatic Rings: 2Heavy Atoms: 28QED Weighted: 0.56Np Likeness Score: -1.05

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