ethyl 6-acetyl-3-(2-acetamidoethyl)-5-methoxy-1H-indole-1-carboxylate

• ChemBase ID: 159190
• Molecular Formular: C18H22N2O5
• Molecular Mass: 346.37768
• Monoisotopic Mass: 346.15287181
• SMILES: c1(c(cc2c(c1)c(cn2C(=O)OCC)CCNC(=O)C)C(=O)C)OC
• Canonical SMILES: CCOC(=O)n1cc(c2c1cc(C(=O)C)c(c2)OC)CCNC(=O)C
• InChI: InChI=1S/C18H22N2O5/c1-5-25-18(23)20-10-13(6-7-19-12(3)22)15-9-17(24-4)14(11(2)21)8-16(15)20/h8-10H,5-7H2,1-4H3,(H,19,22)
• InChIKey: LDCAAXMIAGUBJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 6-acetyl-3-(2-acetamidoethyl)-5-methoxy-1H-indole-1-carboxylate
• IUPAC Traditional name: ethyl 6-acetyl-3-(2-acetamidoethyl)-5-methoxyindole-1-carboxylate
• Synonyms: 6-Acetyl-3-[2-(acetylamino)ethyl]-5-methoxy-H-indole-1-carboxylic Acid Ethyl Ester; 6-Acetyl-N-caboxylate Melatonin Ethyl Ester

Database IDs

• CAS Number: 188397-05-9
• PubChem SID: 162253325
• PubChem CID: 11772361

CALCULATED PROPERTIES

• Acid pKa: 15.078019
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0011684
• LogD (pH = 7.4): 1.0011685
• Log P: 1.0011685
• Molar Refractivity: 92.3252 cm^3
• Polarizability: 36.642216 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - A171960

Used in the preparation of 6-hydroxymelatonin (H944625), a human metabolite of melatonin (M215000).

REFERENCES

• Karam, O. et al.: Tetrahedron Lett. 44, 1511 (2003)