(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-[4-hydroxy-3-(2H3)methoxyphenyl]prop-2-enamide

• ChemBase ID: 168947
• Molecular Formular: C20H20N2O4
• Molecular Mass: 352.3838
• Monoisotopic Mass: 352.14230713
• SMILES: c1(ccc2c(c1)c(c[nH]2)CCNC(=O)/C=C/c1cc(c(cc1)O)OC)O
• Canonical SMILES: COc1cc(/C=C/C(=O)NCCc2c[nH]c3c2cc(O)cc3)ccc1O
• InChI: InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
• InChIKey: WGHKJYWENWLOMY-XVNBXDOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-[4-hydroxy-3-(^2H₃)methoxyphenyl]prop-2-enamide
• IUPAC Traditional name: (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-[4-hydroxy-3-(^2H₃)methoxyphenyl]prop-2-enamide
• Synonyms: N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-[4-hydroxy-3-(methoxy-d3)phenyl]-2-propenamide; N-Feruloylserotonin-d3; NSC 369502-d3; N-Feruloyl Serotonin-d3

Database IDs

• PubChem SID: 162263079
• PubChem CID: 71316750

CALCULATED PROPERTIES

• Acid pKa: 9.390568
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.8998363
• LogD (pH = 7.4): 2.8955164
• Log P: 2.899914
• Molar Refractivity: 100.6579 cm^3
• Polarizability: 39.09575 Å^3
• Polar Surface Area: 94.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F309002

Labelled N-Feruloylserotonin, a conjugated serotonin compound that has been identified as the antioxidative component from the seed of Carthamus tinctorius. N-Feruloylserotonin displayed protective effects on oxidative damage in rat pheochromocytoma cells

REFERENCES

• Baek, N.-I., Han. Nong. Hakh., 42, 366 (1999)
• Piga, R. et al.: Br. J. Nutrit., 103, 25 (1999)
• Kim, E.-O. et al.: Food Sci. Biotechnol., 16, 71 (1999)