CHEBI:77154 - ginsenoside Rc

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ChEBI Name ginsenoside Rc
ChEBI ID CHEBI:77154
Definition A ginsenoside found in Panax ginseng 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 α-L-arabinofuranosyl-(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)22-68-45-41(65)36(60)28(21-56)69-45)24-11-16-52(7)33(24)25(57)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)35(59)27(20-55)71-48)74-46-42(66)38(62)34(58)26(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 JDCPEKQWFDWQLI-LUQKBWBOSA-N
SMILES CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](CO)[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
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ginsenoside Rc (CHEBI:77154) has parent hydride dammarane (CHEBI:36488)
ginsenoside Rc (CHEBI:77154) has role hypoglycemic agent (CHEBI:35526)
ginsenoside Rc (CHEBI:77154) has role plant metabolite (CHEBI:76924)
ginsenoside Rc (CHEBI:77154) is a β-D-glucoside (CHEBI:22798)
ginsenoside Rc (CHEBI:77154) is a 12β-hydroxy steroid (CHEBI:36847)
ginsenoside Rc (CHEBI:77154) is a disaccharide derivative (CHEBI:63353)
ginsenoside Rc (CHEBI:77154) is a ginsenoside (CHEBI:74978)
ginsenoside Rc (CHEBI:77154) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name
(3β,12β)-20-{[6-O-(α-L-arabinofuranosyl)-β-D-glucopyranosyl]oxy}-12-hydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
Synonyms Sources
(20S)-ginsenoside Rc UniProt
NSC 310104 ChemIDplus
Panaxoside RC ChemIDplus
Manual Xrefs Databases
CPD-15452 MetaCyc
HMDB0034995 HMDB
WO2006001654 Patent
View more database links
Registry Numbers Types Sources
11021-14-0 CAS Registry Number ChemIDplus
1677618 Beilstein Registry Number ChemIDplus
6888731 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17268094 PubMed citation Europe PMC
19961916 PubMed citation Europe PMC
23224374 PubMed citation Europe PMC
23411022 PubMed citation Europe PMC
23568202 PubMed citation Europe PMC
23918648 PubMed citation Europe PMC
24013032 PubMed citation Europe PMC
Last Modified
25 March 2024
General Comment
2014-02-11 See also: Yu, H., Liu, Q., Zhang, C., Lu, M., Fu, Y., Im, W.-T., Lee, S.-T. and Jin, F. A new ginsenosidase from Aspergillus strain hydrolyzing 20-O-multi-glycoside of PPD ginsenoside. Process Biochem. 44 (2009) 772-775.