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CHEBI:132749 - (S)-nandinine

ChEBI IDCHEBI:132749
ChEBI Name(S)-nandinine
Stars
ASCII Name(S)-nandinine
DefinitionA 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.
Last Modified16 January 2017
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC19H19NO4
Net Charge0
Average Mass325.364
Monoisotopic Mass325.13141
SMILES[H][C@@]12Cc3ccc(OC)c(O)c3CN1CCc1cc3c(cc12)OCO3
InChIInChI=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
InChIKeyPQECCKIOFCWGRJ-HNNXBMFYSA-N
Species of MetaboliteComponentSourceComments
Eschscholzia californica (ncbitaxon:3467) - PubMed (17250743)
Argemone mexicana (ncbitaxon:54796) - PubMed (21094631)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
(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  Source
(+)-NandininChemIDplus
(+)-nandinineChEBI
S-TetrahydroberberrubineChemIDplus
10-Methoxy-2,3-(methylenedioxy)berbin-9-olChemIDplus
NandinineChemIDplus
(+)-TetrahydroberberrubineChemIDplus
UniProt Name  Source
(S)-nandinineUniProt
Manual XrefsDatabases
C21370KEGG COMPOUND
CPD-16783MetaCyc
Registry NumbersSources
Reaxys:21963851Reaxys
CAS:572-76-9ChemIDplus
Citations