1-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one

• ChemBase ID: 128999
• Molecular Formular: C17H19NO5
• Molecular Mass: 317.33646
• Monoisotopic Mass: 317.12632271
• SMILES: O=C1C=CCCN1C(=O)/C=C/c1cc(OC)c(OC)c(OC)c1
• Canonical SMILES: COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(c1OC)OC
• InChI: InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3
• InChIKey: VABYUUZNAVQNPG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one
• IUPAC Traditional name: 1-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2-one; piperlongumine
• Synonyms: Piplartine; Piperlongumine; 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone; (E)-5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone; 5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridone; Piplartin

Database IDs

• CAS Number: 20069-09-4
• PubChem SID: 162223301
• PubChem CID: 637858
• CHEMBL: 465843
• Chemspider ID: 553441
• Wikipedia Title: Piperlongumine

CALCULATED PROPERTIES

• Acid pKa: 17.765062
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.7378093
• LogD (pH = 7.4): 1.7378093
• Log P: 1.7378093
• Molar Refractivity: 87.3239 cm^3
• Polarizability: 32.78375 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P482850

Piperlongumine (PL), a new alkaloid abundantly present in Piper longum fruits strongly inhibited platelet cell aggregation. It may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed.

REFERENCES

• Beretz, A., et al.: Planta Med., 57, 68 (1991)
• Lee, S., et al.: J. Microbiol. Biotechnol., 12, 679 (1991)
• Lee, K., et al.: Pharmacol. Res., 53, 265 (1991)