tert-butyl 3-(2-acetamidoethyl)-5-{[(2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}-1H-indole-1-carboxylate

• ChemBase ID: 159181
• Molecular Formular: C30H38N2O13
• Molecular Mass: 634.62832
• Monoisotopic Mass: 634.23738929
• SMILES: c1(ccc2c(c1)c(cn2C(=O)OC(C)(C)C)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)cn3C(=O)OC(C)(C)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C30H38N2O13/c1-15(33)31-12-11-19-14-32(29(38)45-30(5,6)7)22-10-9-20(13-21(19)22)43-28-26(42-18(4)36)24(41-17(3)35)23(40-16(2)34)25(44-28)27(37)39-8/h9-10,13-14,23-26,28H,11-12H2,1-8H3,(H,31,33)/t23-,24-,25-,26+,28+/m0/s1
• InChIKey: RSLJLPFHYCLDBE-YYDZWWTMSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253316
• PubChem CID: 71312844

CALCULATED PROPERTIES

• Acid pKa: 15.3438835
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.5162551
• LogD (pH = 7.4): 1.5162554
• Log P: 1.5162554
• Molar Refractivity: 150.7325 cm^3
• Polarizability: 61.91149 Å^3
• Polar Surface Area: 183.99 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A171160

Protected Malatonin metabolite.