Alstonine
Basic information
- CAS
642-18-2- Standard SMILES
COC(=O)C1=CO[C@@H](C)[C@@H]2Cn3ccc4c5ccccc5nc-4c3C[C@H]12- InChIKey
WYTGDNHDOZPMIW-RCBQFDQVSA-N- Molecular formula
- C21H20N2O3
- Average molar mass
- 348.4 g/mol
- Monoisotopic mass
- 348.1473925
Overview
Alstonine is an indole alkaloid with formula C21H20N2O3, isolated from several Rauvolfia species and exhibits antipsychotic activity. It has a role as an antipsychotic agent. It is a methyl ester, a zwitterion, an organic heteropentacyclic compound and an indole alkaloid. It is a conjugate base of an alstonine(1+).
Names & identifiers
- Preferred name
- Alstonine
- IUPAC
- methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate
- English name
- Indole alkaloid
- Molecular formula
- C21H20N2O3
- Molecular weight
- 348.4
Names & synonyms
ALSTONINE642-18-2SB0M27Q90XUNII-SB0M27Q90X3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19alpha-methyl-20alpha-oxayohimbanium(4S,4aS,14aS)-1-(methoxycarbonyl)-4-methyl-4a,5,14,14a-tetrahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizin-6-ium-13-ideNCI60_041680C09028alstonin20alpha-Oxayohimbanium, 3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19alpha-methyl-methyl (15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylateAC1L9C1H
Show more names
Aids002662Aids-0026623,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19.alpha.-methyl-20.alpha.- oxayohimbaniumOxayohimbanium,3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyl-, inner salt, (19a,20a)-
ALSTONINE [MI]CHEBI:2612CHEMBL1187439SCHEMBL29363751Alstonine, hydroxide, inner saltWYTGDNHDOZPMIW-RCBQFDQVSA-NDTXSID201115727BDBM50480268
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 53.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 606
Physicochemical properties
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- Solid
- color
- White to yellow
- FDA UNII
- 0 M27Q90X · SB0M27Q90X
Chemistry & industry
Applications
UsesAlstonine is a major indole alkaloid compound of a plant-based remedy. Alstonine has antipsychotic, anxiolytic, anticancer and antimalarial properties[1].
Additional notes
DefinitionChEBI: Alstonine is an indole alkaloid with formula C21H20N2O3, isolated from several Rauvolfia species and exhibits antipsychotic activity. It has a role as an antipsychotic agent. It is a methyl ester, an organic heteropentacyclic compound, a zwitterion and an indole alkaloid. It is a conjugate base of an alstonine(1+).
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