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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
28 29 0 0 0 0 0 0 0 0999 V2000
2.7777 -15.7458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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
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
13 8 1 0
26 27 1 0
26 28 2 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Calculated Properties Molecular Weight: 394.31Molecular Weight (Monoisotopic): 394.0777AlogP: 3.73#Rotatable Bonds: 6Polar 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: -2.01Aromatic 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 ]