CHEBI:65632 - cimifoetiside A

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ChEBI Name cimifoetiside A
ChEBI ID CHEBI:65632
Definition A triterpene glycoside that consists of cimigenol attached to a β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl moiety at position 3 via a β-glycosidic linkage (the 23R,24S stereoisomer). It is isolated from the aerial parts of Cimicifuga foetida and exhibits significant immunosuppressive effect.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C41H66O14
Net Charge 0
Average Mass 782.95430
Monoisotopic Mass 782.44526
InChI InChI=1S/C41H66O14/c1-18-14-20-31(36(4,5)49)55-41(54-20)30(18)37(6)12-13-40-17-39(40)11-10-24(35(2,3)22(39)8-9-23(40)38(37,7)34(41)48)52-32-28(47)29(19(43)16-50-32)53-33-27(46)26(45)25(44)21(15-42)51-33/h18-34,42-49H,8-17H2,1-7H3/t18-,19-,20-,21-,22+,23+,24+,25-,26+,27-,28-,29+,30-,31+,32+,33+,34-,37-,38-,39-,40+,41+/m1/s1
InChIKey LANJQSWIMVURCX-CXSVBUCUSA-N
SMILES [H][C@@]12C[C@@H](C)[C@]3([H])[C@@]4(C)CC[C@@]56C[C@@]55CC[C@H](O[C@]7([H])OC[C@@H](O)[C@H](O[C@]8([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)C(C)(C)[C@]5([H])CC[C@@]6([H])[C@]4(C)[C@@H](O)[C@]3(O[C@@H]1C(C)(C)O)O2
Metabolite of Species Details
Cimicifuga foetida (NCBI:txid64032) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Biological Role(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cimifoetiside A (CHEBI:65632) has functional parent cimigenol (CHEBI:37777)
cimifoetiside A (CHEBI:65632) has parent hydride cycloartane (CHEBI:37778)
cimifoetiside A (CHEBI:65632) has role immunosuppressive agent (CHEBI:35705)
cimifoetiside A (CHEBI:65632) has role plant metabolite (CHEBI:76924)
cimifoetiside A (CHEBI:65632) is a bridged compound (CHEBI:35990)
cimifoetiside A (CHEBI:65632) is a diol (CHEBI:23824)
cimifoetiside A (CHEBI:65632) is a disaccharide derivative (CHEBI:63353)
cimifoetiside A (CHEBI:65632) is a oxacycle (CHEBI:38104)
cimifoetiside A (CHEBI:65632) is a secondary alcohol (CHEBI:35681)
cimifoetiside A (CHEBI:65632) is a tertiary alcohol (CHEBI:26878)
cimifoetiside A (CHEBI:65632) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(2S,4aR,5aS,7aR,7bR,8R,10R,11S,12aS,13R,13aS,13bR,15aR)-13-hydroxy-11-(2-hydroxypropan-2-yl)-1,1,7a,8,13a-pentamethyloctadecahydro-10,12a-epoxycyclopropa[1',8a']naphtho[2',1':4,5]indeno[2,1-b]oxepin-2-yl 3-O-β-D-glucopyranosyl-β-D-xylopyranoside
Synonym Source
(23R,24S) cimicigenol 3-O-β-D-glucopyranosyl-(1→3)-β-D-xylopyranoside ChEBI
Citation Waiting for Citations Type Source
19280146 PubMed citation Europe PMC
Last Modified
20 January 2014