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

• ChemBase ID: 163786
• Molecular Formular: C16H20N2O5
• Molecular Mass: 320.3404
• Monoisotopic Mass: 320.13722175
• SMILES: c1(c(cc2c(c1)c(cn2C(=O)OCC)CCNC(=O)C)O)OC
• Canonical SMILES: CCOC(=O)n1cc(c2c1cc(O)c(c2)OC)CCNC(=O)C
• InChI: InChI=1S/C16H20N2O5/c1-4-23-16(21)18-9-11(5-6-17-10(2)19)12-7-15(22-3)14(20)8-13(12)18/h7-9,20H,4-6H2,1-3H3,(H,17,19)
• InChIKey: UTTBAHIPNUITES-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162257921
• PubChem CID: 71314551

CALCULATED PROPERTIES

• Acid pKa: 9.128761
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.1398542
• LogD (pH = 7.4): 1.131981
• Log P: 1.1399556
• Molar Refractivity: 83.9033 cm^3
• Polarizability: 33.51159 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - C179790

Used in the preparation of 6-Sulfatoxy Melatonin Sodium Salt (S689050), a metabolite of Melatonin (M215000).