CHEBI:9271 - stevioside

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ChEBI Name stevioside
ChEBI ID CHEBI:9271
Definition A diterpene glycoside that is rubusoside in which the hydroxy group at position 2 of the allylic β-D-glucoside has been converted to the corresponding β-D-glucoside. It is a natural herbal sweetener that is 250-300 times sweeter than sucrose (though with a bitter aftertaste), extracted from the Stevia rebaudiana plant native to South America.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9333161, eMolecules:514736, ZINC000006920380
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Formula C38H60O18
Net Charge 0
Average Mass 804.880
Monoisotopic Mass 804.37797
InChI InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1
InChIKey UEDUENGHJMELGK-HYDKPPNVSA-N
SMILES O([C@@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CO)C([C@]2([C@@]3([C@]([C@]4([C@]5(C[C@@](CC4)(C(C5)=C)O[C@H]6[C@H](O[C@@H]7O[C@@H]([C@@H](O)[C@@H]([C@H]7O)O)CO)[C@H]([C@H](O)[C@H](O6)CO)O)CC3)[H])(CCC2)C)[H])C)=O
Metabolite of Species Details
Stevia rebaudiana (NCBI:txid55670) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): sweetening agent
Substance that sweeten food, beverages, medications, etc.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): sweetening agent
Substance that sweeten food, beverages, medications, etc.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
hypoglycemic agent
A drug which lowers the blood glucose level.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing stevioside (CHEBI:9271) has functional parent rubusoside (CHEBI:145021)
stevioside (CHEBI:9271) has functional parent steviol (CHEBI:145024)
stevioside (CHEBI:9271) has role anti-inflammatory agent (CHEBI:67079)
stevioside (CHEBI:9271) has role antineoplastic agent (CHEBI:35610)
stevioside (CHEBI:9271) has role antioxidant (CHEBI:22586)
stevioside (CHEBI:9271) has role hypoglycemic agent (CHEBI:35526)
stevioside (CHEBI:9271) has role plant metabolite (CHEBI:76924)
stevioside (CHEBI:9271) has role sweetening agent (CHEBI:50505)
stevioside (CHEBI:9271) is a β-D-glucoside (CHEBI:22798)
stevioside (CHEBI:9271) is a ent-kaurane diterpenoid (CHEBI:36760)
stevioside (CHEBI:9271) is a bridged compound (CHEBI:35990)
stevioside (CHEBI:9271) is a diterpene glycoside (CHEBI:71939)
stevioside (CHEBI:9271) is a tetracyclic diterpenoid (CHEBI:52557)
Incoming rebaudioside E (CHEBI:145018) has functional parent stevioside (CHEBI:9271)
IUPAC Name
1-O-{13α-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-18-oxo-5β,8α,9β,10α-kaur-16-en-18-yl}-β-D-glucopyranose
Synonyms Sources
13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-D-glucopyranosyl ester ChEBI
stevioside KEGG COMPOUND
stevioside UniProt
steviosin ChemIDplus
Manual Xrefs Databases
C00003485 KNApSAcK
C09189 KEGG COMPOUND
CPD-14504 MetaCyc
FDB013538 FooDB
HMDB0034945 HMDB
Stevioside Wikipedia
View more database links
Registry Number Type Source
57817-89-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14561506 PubMed citation Europe PMC
15610349 PubMed citation Europe PMC
28363166 PubMed citation Europe PMC
30319406 PubMed citation Europe PMC
30735218 PubMed citation Europe PMC
30820204 PubMed citation Europe PMC
30890404 PubMed citation Europe PMC
31020296 PubMed citation Europe PMC
31075241 PubMed citation Europe PMC
31182573 PubMed citation Europe PMC
IND606343899 Agricola citation Europe PMC
Last Modified
08 October 2019