stepharanine (CHEBI:132718)

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ChEBI Name	stepharanine

ChEBI ID	CHEBI:132718

Definition	A berberine alkaloid with formula C₁₉H₁₈NO₄ that is isolated from several species of Stephania.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	qingping liu

Supplier Information

Download	Molfile XML SDF

Formula

C19H18NO4

Net Charge

Average Mass

324.351

Monoisotopic Mass

324.12303

InChI

InChI=1S/C19H17NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,7-10H,5-6H2,1-2H3,(H-,21,22)/p+1

InChIKey

BENXORZPKXUGMY-UHFFFAOYSA-O

SMILES

O(C=1C2=C[N+]=3CCC=4C(C3C=C2C=CC1O)=CC(O)=C(OC)C4)C

Metabolite of Species	Details
Stephania dentifolia (NCBI:txid1501456)	Found in root (BTO:0001188). See: PubMed
Tinospora capillipes (NCBI:txid150903)	Found in root (BTO:0001188). See: PubMed
Corydalis yanhusuo (NCBI:txid458692)	See: PubMed
Stephania venosa (NCBI:txid527508)	Found in tuber (BTO:0001400). See: PubMed
Xylopia parviflora (NCBI:txid992813)	Found in bark (BTO:0001301). See: PubMed
Xylopia parviflora (NCBI:txid992813)	Found in root (BTO:0001188). See: PubMed

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 3.1.1.7 (acetylcholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. 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	stepharanine (CHEBI:132718) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462) stepharanine (CHEBI:132718) has role plant metabolite (CHEBI:76924) stepharanine (CHEBI:132718) is a berberine alkaloid (CHEBI:22754) stepharanine (CHEBI:132718) is a organic cation (CHEBI:25697) stepharanine (CHEBI:132718) is a organic heterotetracyclic compound (CHEBI:38163)

IUPAC Name

2,10-dihydroxy-3,9-dimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium

Synonym	Source
Stepharanin	KNApSAcK

Last Modified

16 January 2017