(2S,3S,4S,5R,6S)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159450
• Molecular Formular: C18H22N2O8
• Molecular Mass: 394.37588
• Monoisotopic Mass: 394.13761567
• SMILES: c1(ccc2c(c1)c(c[nH]2)CCNC(=O)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CC(=O)NCCc1c[nH]c2c1cc(cc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H22N2O8/c1-8(21)19-5-4-9-7-20-12-3-2-10(6-11(9)12)27-18-15(24)13(22)14(23)16(28-18)17(25)26/h2-3,6-7,13-16,18,20,22-24H,4-5H2,1H3,(H,19,21)(H,25,26)/t13-,14-,15+,16-,18+/m0/s1
• InChIKey: DRKQFNYKSNWOTC-RNGZQALNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-[2-(Acetylamino)ethyl]-1H-indol-5-yl-β-D-glucopyranosiduronic Acid; N-Acetyl Serotonin β-D-Glucuronide

Database IDs

• CAS Number: 18430-06-3
• PubChem SID: 162253585
• PubChem CID: 29971054

CALCULATED PROPERTIES

• Acid pKa: 3.3185654
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.1113203
• LogD (pH = 7.4): -4.368189
• Log P: -0.94607484
• Molar Refractivity: 93.8094 cm^3
• Polarizability: 38.29167 Å^3
• Polar Surface Area: 161.34 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Tan Solid
• Melting Point: 128-131°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A187790

A metabolite of Malatonin.

REFERENCES

• Young, I., et al.: J. Clin. Endocrinol. Metab., 60, 114 (1985)
• Barrenetxe, J., et al.: J. Physiol. Biochem., 60, 61 (1985)