CHEBI:77153 - ginsenoside Rb3

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ChEBI Name ginsenoside Rb3
Definition A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3β, 12β and 20 pro-S positions, in which the hydroxy groups at positions 3 and 20 have been converted to the corresponding β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside and β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
Supplier Information
Download Molfile XML SDF
Formula C53H90O22
Net Charge 0
Average Mass 1079.26850
Monoisotopic Mass 1078.59237
InChI InChI=1S/C53H90O22/c1-23(2)10-9-14-53(8,75-47-43(67)39(63)37(61)29(72-47)22-69-45-41(65)34(58)26(57)21-68-45)24-11-16-52(7)33(24)25(56)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)36(60)28(20-55)71-48)74-46-42(66)38(62)35(59)27(19-54)70-46/h10,24-48,54-67H,9,11-22H2,1-8H3/t24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-,46-,47-,48-,50-,51+,52+,53-/m0/s1
SMILES CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@@]21C
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ginsenoside Rb3 (CHEBI:77153) has parent hydride dammarane (CHEBI:36488)
ginsenoside Rb3 (CHEBI:77153) has role antidepressant (CHEBI:35469)
ginsenoside Rb3 (CHEBI:77153) has role antioxidant (CHEBI:22586)
ginsenoside Rb3 (CHEBI:77153) has role cardioprotective agent (CHEBI:77307)
ginsenoside Rb3 (CHEBI:77153) has role neuroprotective agent (CHEBI:63726)
ginsenoside Rb3 (CHEBI:77153) has role NMDA receptor antagonist (CHEBI:60643)
ginsenoside Rb3 (CHEBI:77153) has role plant metabolite (CHEBI:76924)
ginsenoside Rb3 (CHEBI:77153) is a β-D-glucoside (CHEBI:22798)
ginsenoside Rb3 (CHEBI:77153) is a 12β-hydroxy steroid (CHEBI:36847)
ginsenoside Rb3 (CHEBI:77153) is a disaccharide derivative (CHEBI:63353)
ginsenoside Rb3 (CHEBI:77153) is a ginsenoside (CHEBI:74978)
ginsenoside Rb3 (CHEBI:77153) is a tetracyclic triterpenoid (CHEBI:26893)
(3β,12β)-20-{[6-O-(β-D-xylopyranosyl)-β-D-glucopyranosyl]oxy}-12-hydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
Synonym Source
ginsenoside Rb3 UniProt
Manual Xrefs Databases
CN101390887 Patent
CN101856365 Patent
CPD-15453 MetaCyc
KR20120001996 Patent
View more database links
Registry Numbers Types Sources
5724307 Reaxys Registry Number Reaxys
68406-26-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19655413 PubMed citation Europe PMC
20371232 PubMed citation Europe PMC
20662827 PubMed citation Europe PMC
20969942 PubMed citation Europe PMC
21158074 PubMed citation Europe PMC
21186573 PubMed citation Europe PMC
21591990 PubMed citation Europe PMC
21948936 PubMed citation Europe PMC
Last Modified
11 February 2014