ginsenoside Rb3 (CHEBI:77153)

EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:77153 - ginsenoside Rb3

Take structure to advanced search

ChEBI ID	CHEBI:77153
ChEBI Name	ginsenoside Rb3
Stars
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.
Last Modified	11 February 2014
Submitter	KAX
Downloads	Molfile

Formula	C53H90O22
Net Charge	0
Average Mass	1079.281
Monoisotopic Mass	1078.59237
SMILES	[H][C@]12C[C@@H](O)[C@]3([H])[C@@]([H])([C@](C)(CCC=C(C)C)O[C@@H]4O[C@H](CO[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]21C
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
InChIKey	NODILNFGTFIURN-USYOXQFSSA-N

Roles Classification

Chemical Role:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:	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. 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.
Applications:	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. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

ChEBI Ontology

Outgoing Relation(s)
	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 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)
	ginsenoside Rb3 (CHEBI:77153) is a β-D-glucoside (CHEBI:22798)

IUPAC Name
(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

UniProt Name	Source
ginsenoside Rb3	UniProt

Manual Xrefs	Databases
CPD-15453	MetaCyc
KR20120001996	Patent
CN101856365	Patent
CN101390887	Patent

Registry Numbers	Sources
Reaxys:5724307	Reaxys
CAS:68406-26-8	ChemIDplus

Citations