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ID: ALA270911
PubChem CID: 44457087
Max Phase: Preclinical
Molecular Formula: C18H13F3N2O5
Molecular Weight: 394.31
Molecule Type: Small molecule
Associated Items:
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
Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
---|
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 |
Molecular Weight: 394.31 | Molecular Weight (Monoisotopic): 394.0777 | AlogP: 3.73 | #Rotatable Bonds: 6 |
Polar Surface Area: 115.73 | Molecular Species: ACID | HBA: 4 | HBD: 4 |
#RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 2.88 | CX Basic pKa: ┄ | CX LogP: 4.67 | CX LogD: -2.01 |
Aromatic Rings: 2 | Heavy Atoms: 28 | QED Weighted: 0.56 | Np Likeness Score: -1.05 |
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] |
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