EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:2612 - alstonine

Default Structure
ChEBI IDCHEBI:2612
ChEBI Namealstonine
Stars
DefinitionAn indole alkaloid with formula C21H20N2O3, isolated from several Rauvolfia species and exhibits antipsychotic activity.
Last Modified16 November 2018
DownloadsMolfile
FormulaC21H20N2O3
Net Charge0
Average Mass348.402
Monoisotopic Mass348.14739
SMILES[H][C@@]12C[n+]3ccc4c([n-]c5ccccc54)c3C[C@]1([H])C(C(=O)OC)=CO[C@H]2C
InChIInChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16-/m0/s1
InChIKeyWYTGDNHDOZPMIW-RCBQFDQVSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Rauvolfia hirsuta (IPNI:INI81548-1) root (BTO:0001188) Article (Vergara, B.U. (1955) Extraction of reserpine and other alkaloids from Colombian Rauwolfia hirsute. J. Am. Chem. Soc., 77(7), 1864-1864.)
Rauvolfia obscura (IPNI:81602-1)
root (BTO:0001188) PubMed (948531)
leaf (BTO:0000713) PubMed (1121522)
Rauvolfia volkensii (IPNI:81672-1) root (BTO:0001188) PubMed (7253681)
Rauvolfia vomitoria (IPNI:81673-1) - Article (Schlittler, E., Schwarz, H. and Bader, F. (1952) Isolierung von Alstonin aus afrikanischen Rauwolfia‐Arten. Helv. Chim. Acta, 35(1), 271-276.)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
ChEBI Ontology
Outgoing Relation(s)
alstonine (CHEBI:2612) has role antipsychotic agent (CHEBI:35476)
alstonine (CHEBI:2612) is a indole alkaloid (CHEBI:38958)
alstonine (CHEBI:2612) is a methyl ester (CHEBI:25248)
alstonine (CHEBI:2612) is a organic heteropentacyclic compound (CHEBI:38164)
alstonine (CHEBI:2612) is a zwitterion (CHEBI:27369)
alstonine (CHEBI:2612) is conjugate base of alstonine(1+) (CHEBI:142530)
Incoming Relation(s)
alstonine(1+) (CHEBI:142530) is conjugate acid of alstonine (CHEBI:2612)
IUPAC Name 
(19α,20α)-16-(methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide
Synonyms  Source
3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19α-methyl-20α-oxayohimbaniumChEBI
alstoninChEBI
alstonineKEGG COMPOUND
Manual XrefsDatabases
AlstonineWikipedia
C00001683KNApSAcK
C09028KEGG COMPOUND
Registry NumbersSources
CAS:642-18-2ChemIDplus
CAS:642-18-2KEGG COMPOUND
Citations