methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 159461
• Molecular Formular: C25H30N2O11
• Molecular Mass: 534.5125
• Monoisotopic Mass: 534.18495979
• 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)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)c(CCNC(=O)C)c[nH]3)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H30N2O11/c1-12(28)26-9-8-16-11-27-19-7-6-17(10-18(16)19)37-25-23(36-15(4)31)21(35-14(3)30)20(34-13(2)29)22(38-25)24(32)33-5/h6-7,10-11,20-23,25,27H,8-9H2,1-5H3,(H,26,28)/t20-,21-,22-,23+,25+/m0/s1
• InChIKey: ARTSFIBYNZSGDU-FPDJOHNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylate
• Synonyms: 3-[2-(Acetylamino)ethyl]-1H-indol-5-yl-tri-O-acetyl-β-D-glucopyranosiduronic Acid Methyl Ester; N-Acetyl Serotonin Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 162253596
• PubChem CID: 71312995

CALCULATED PROPERTIES

• Acid pKa: 15.36671
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.5231953
• LogD (pH = 7.4): 0.52319545
• Log P: 0.52319545
• Molar Refractivity: 126.033 cm^3
• Polarizability: 51.922718 Å^3
• Polar Surface Area: 168.55 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethylformamide; Methanol
• Apperance: Off-White Foam

DETAILS

Toronto Research Chemicals - A187830

Protected Malatonin metabolite.