CHEBI:132749 - (S)-nandinine

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ChEBI Name (S)-nandinine
ChEBI ASCII Name (S)-nandinine
Definition A berberine alkaloid that is 5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline carrying hydroxy and methoxy substituents at positions 9 and 10 respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C19H19NO4
Net Charge 0
Average Mass 325.359
Monoisotopic Mass 325.13141
InChI InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
SMILES N12[C@](C3=C(CC1)C=C4C(=C3)OCO4)(CC5=C(C2)C(=C(C=C5)OC)O)[H]
Metabolite of Species Details
Eschscholzia californica (NCBI:txid3467) See: PubMed
Argemone mexicana (NCBI:txid54796) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): anti-obesity agent
Any substance which is used to reduce or control weight.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-nandinine (CHEBI:132749) has role anti-obesity agent (CHEBI:74518)
(S)-nandinine (CHEBI:132749) has role plant metabolite (CHEBI:76924)
(S)-nandinine (CHEBI:132749) is a aromatic ether (CHEBI:35618)
(S)-nandinine (CHEBI:132749) is a berberine alkaloid (CHEBI:22754)
(S)-nandinine (CHEBI:132749) is a organic heteropentacyclic compound (CHEBI:38164)
(S)-nandinine (CHEBI:132749) is a phenols (CHEBI:33853)
(S)-nandinine (CHEBI:132749) is a tertiary amino compound (CHEBI:50996)
Incoming (S)-canadine (CHEBI:16592) has functional parent (S)-nandinine (CHEBI:132749)
Synonyms Sources
(+)-Nandinin ChemIDplus
(+)-nandinine ChEBI
(+)-Tetrahydroberberrubine ChemIDplus
(S)-nandinine UniProt
10-Methoxy-2,3-(methylenedioxy)berbin-9-ol ChemIDplus
Nandinine ChemIDplus
S-Tetrahydroberberrubine ChemIDplus
Manual Xrefs Databases
CPD-16783 MetaCyc
View more database links
Registry Numbers Types Sources
21963851 Reaxys Registry Number Reaxys
572-76-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17250743 PubMed citation SUBMITTER
21094631 PubMed citation SUBMITTER
27462872 PubMed citation Europe PMC
28085967 PubMed citation Europe PMC
618457 Chinese Abstracts citation Europe PMC
Last Modified
16 January 2017