CHEBI:132718 - stepharanine

ChEBI IDCHEBI:132718
ChEBI Namestepharanine
Stars
DefinitionA berberine alkaloid with formula C19H18NO4 that is isolated from several species of Stephania.
Last Modified16 January 2017
Submitterliuqingping
DownloadsMolfile
FormulaC19H18NO4
Net Charge+1
Average Mass324.356
Monoisotopic Mass324.12303
SMILESCOc1cc2c(cc1O)-c1cc3ccc(O)c(OC)c3c[n+]1CC2
InChIInChI=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
InChIKeyBENXORZPKXUGMY-UHFFFAOYSA-O
Species of MetaboliteComponentSourceComments
Corydalis yanhusuo (ncbitaxon:458692) - PubMed (22737858)
Stephania dentifolia (ncbitaxon:1501456) root (BTO:0001188) PubMed (23713286)
Tinospora capillipes (ncbitaxon:150903) root (BTO:0001188) PubMed (17340259)
Stephania venosa (ncbitaxon:527508) tuber (BTO:0001400) PubMed (16640839)
Xylopia parviflora (ncbitaxon:992813)
root (BTO:0001188) PubMed (15081299)
bark (BTO:0001301) PubMed (15081299)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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
StepharaninKNApSAcK
Manual XrefsDatabases
10358881PubChem Compound
C00026048KNApSAcK
Registry NumbersSources
Reaxys:1554249Reaxys
CAS:17369-30-1KNApSAcK
Citations