(S)-nandinine (CHEBI:132749)

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ChEBI Name	(S)-nandinine

ChEBI ID	CHEBI:132749

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

Download	Molfile XML SDF

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Formula

C19H19NO4

Net Charge

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

InChIKey

PQECCKIOFCWGRJ-HNNXBMFYSA-N

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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

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)

IUPAC Name

(13aS)-10-methoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-9-ol

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

Last Modified

16 January 2017