CHEBI:2612 - alstonine

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ChEBI Name alstonine
ChEBI ID CHEBI:2612
Definition An indole alkaloid with formula C21H20N2O3, isolated from several Rauvolfia species and exhibits antipsychotic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H20N2O3
Net Charge 0
Average Mass 348.396
Monoisotopic Mass 348.14739
InChI InChI=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
InChIKey WYTGDNHDOZPMIW-RCBQFDQVSA-N
SMILES C=1C=CC2=C(C1)C=3C=C[N+]4=C(C3[N-]2)C[C@]5([C@]([C@@H](OC=C5C(OC)=O)C)(C4)[H])[H]
Metabolite of Species Details
Rauvolfia obscura (IPNI:81602-1) Found in root (BTO:0001188). See: PubMed
Rauvolfia obscura (IPNI:81602-1) Found in leaf (BTO:0000713). See: PubMed
Rauvolfia volkensii (IPNI:81672-1) Found in root (BTO:0001188). See: PubMed
Rauvolfia vomitoria (IPNI:81673-1) See: Schlittler, E., Schwarz, H. and Bader, F. (1952) Isolierung von Alstonin aus afrikanischen Rauwolfia‐Arten. Helv. Chim. Acta, 35(1), 271-276.
Rauvolfia hirsuta (IPNI:INI81548-1) Found in root (BTO:0001188). See: Vergara, B.U. (1955) Extraction of reserpine and other alkaloids from Colombian Rauwolfia hirsute. J. Am. Chem. Soc., 77(7), 1864-1864.
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
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ChEBI Ontology
Outgoing 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 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 Sources
3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19α-methyl-20α-oxayohimbanium ChEBI
alstonin ChEBI
alstonine KEGG COMPOUND
Manual Xrefs Databases
Alstonine Wikipedia
C00001683 KNApSAcK
C09028 KEGG COMPOUND
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Registry Number Type Source
642-18-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10412490 PubMed citation Europe PMC
15006458 PubMed citation Europe PMC
16550222 PubMed citation Europe PMC
18539376 PubMed citation Europe PMC
19189988 PubMed citation Europe PMC
20241896 PubMed citation Europe PMC
21925231 PubMed citation Europe PMC
22940693 PubMed citation Europe PMC
6074294 PubMed citation Europe PMC
9610935 PubMed citation Europe PMC
Last Modified
16 November 2018