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

• ChemBase ID: 163785
• Molecular Formular: C18H22N2O6
• Molecular Mass: 362.37708
• Monoisotopic Mass: 362.14778643
• SMILES: c1(c(cc2c(c1)c(cn2C(=O)OCC)CCNC(=O)C)OC(=O)C)OC
• Canonical SMILES: CCOC(=O)n1cc(c2c1cc(OC(=O)C)c(c2)OC)CCNC(=O)C
• InChI: InChI=1S/C18H22N2O6/c1-5-25-18(23)20-10-13(6-7-19-11(2)21)14-8-16(24-4)17(9-15(14)20)26-12(3)22/h8-10H,5-7H2,1-4H3,(H,19,21)
• InChIKey: CAQVWXISGZMXAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 519186-55-1
• PubChem SID: 162257920
• PubChem CID: 11187587

CALCULATED PROPERTIES

• Acid pKa: 15.14052
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0507818
• LogD (pH = 7.4): 1.050782
• Log P: 1.050782
• Molar Refractivity: 93.0548 cm^3
• Polarizability: 37.35206 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Slightly Yellow Solid

DETAILS

Toronto Research Chemicals - C179780

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

REFERENCES

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