N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)(2H4)ethyl]acetamide

• ChemBase ID: 170723
• Molecular Formular: C13H16N2O3
• Molecular Mass: 248.27774
• Monoisotopic Mass: 248.11609238
• SMILES: c1(c(cc2c(c1)c(c[nH]2)CCNC(=O)C)O)OC
• Canonical SMILES: COc1cc2c(CCNC(=O)C)c[nH]c2cc1O
• InChI: InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
• InChIKey: OMYMRCXOJJZYKE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)(^2H₄)ethyl]acetamide
• IUPAC Traditional name: N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)(^2H₄)ethyl]acetamide
• Synonyms: N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide-d4; 6-Hydroxy-N-acetyl-5-methoxytryptamine-d4; 6-Hydroxy Melatonin-d4

Database IDs

• PubChem SID: 164226633
• PubChem CID: 71749111

CALCULATED PROPERTIES

• Acid pKa: 9.2939
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.843978
• LogD (pH = 7.4): 0.8385781
• Log P: 0.8440475
• Molar Refractivity: 68.2608 cm^3
• Polarizability: 27.221521 Å^3
• Polar Surface Area: 74.35 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H944627

A labelled metabolite of Melatonin (S689050).

REFERENCES

• Huether, G., et al.: Life Sci., 51, 945 (1992)
• Holmes, M., et al.: J. Clin. Oncol., 18, 3668 (1992)
• Roth, G., et al.: J. Clin. Endocrinol. Metab., 86, 3292 (1992)