Methyl (2S,3R,4S)-4-(((1R)-2-acetyl-1,2,3,4-tetrahydro-6,7-dihydroxy-1-isoquinolinyl)methyl)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate
Basic information
- CAS
15401-60-2- Standard SMILES
C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1c2cc(O)c(O)cc2CCN1C(C)=O- InChIKey
QISXROCIXKXUPS-OWVLCBNUSA-N- Molecular formula
- C27H35NO12
- Average molar mass
- 565.6 g/mol
- Monoisotopic mass
- 565.21592555
Overview
Ipecoside is a member of acetamides, a beta-D-glucoside, an isoquinoline alkaloid, an isoquinolinol, a methyl ester, a terpene glycoside and an olefinic compound. It has a role as a plant metabolite. It is functionally related to an ipecoside aglycone.
Names & identifiers
- Preferred name
- Methyl (2S,3R,4S)-4-(((1R)-2-acetyl-1,2,3,4-tetrahydro-6,7-dihydroxy-1-isoquinolinyl)methyl)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate
- IUPAC
- methyl (2S,3R,4S)-4-[[(1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
- English name
- AIDS031406
- Molecular formula
- C27H35NO12
- Molecular weight
- 565.57
Names & synonyms
Ipecoside15401-60-2methyl (2S,3R,4S)-4-[[(1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylateMethyl (2S,3R,4S)-4-[[(1R)-2-acetyl-1,2,3,4-tetrahydro-6,7-dihydroxy-1-isoquinolinyl]methyl]-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylateMethyl (2S,3R,4S)-4-(((1R)-2-acetyl-1,2,3,4-tetrahydro-6,7-dihydroxy-1-isoquinolinyl)methyl)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylatemethyl (2S,3R,4S)-4-(((1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl)methyl)-3-ethenyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,4-dihydro-2H-pyran-5-carboxylateRefChem:148627CHEBI:5952MEGxp0_001513orb1220769orb1301527SCHEMBL5156171
Show more names
AIDS031406NSC 603972Ipecoside, 10 mM in DMSO
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 196 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 8
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 960
Physicochemical properties
- Melting point
- 175 °C · 175 °C (approx)
- Boiling point
- 821.6 · 821.6±65.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- pka
- 9.53 · 9.53±0.40(Predicted)
- form
- Solid
- color
- Off-white to light yellow
Chemistry & industry
Applications
UsesIpecoside is an alkaloid isolated from Psychotria[1].
Additional notes
DefinitionChEBI: Ipecoside is a terpene glycoside.
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