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

• ChemBase ID: 165002
• Molecular Formular: C19H18N2O3
• Molecular Mass: 322.35782
• Monoisotopic Mass: 322.13174245
• SMILES: c1c(cc2c(c1)[nH]cc2CCNC(=O)/C=C/c1ccc(cc1)O)O
• Canonical SMILES: O=C(/C=C/c1ccc(cc1)O)NCCc1c[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+
• InChIKey: WLZPAFGVOWCVMG-FPYGCLRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
• IUPAC Traditional name: (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
• Synonyms: N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)-2-propenamide; NSC 369503; p-Coumaroylserotonin; N-(p-Coumaroyl) Serotonin

Database IDs

• CAS Number: 68573-24-0
• PubChem SID: 162259135
• PubChem CID: 5458879

CALCULATED PROPERTIES

• Acid pKa: 9.181925
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): 3.0574732
• LogD (pH = 7.4): 3.0504827
• Log P: 3.0575855
• Molar Refractivity: 94.1947 cm^3
• Polarizability: 36.587364 Å^3
• Polar Surface Area: 85.35 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Tan Solid
• Melting Point: 192-194°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C756300

Antibacterial agent.

REFERENCES

• Gribble, G.W., et al.: J. Med. Chem., 31, 1746 (1988)
• Maeda, U., et al.: Phytochemistry, 34, 1633 (1988)