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CHEBI:65632 - cimifoetiside A

ChEBI IDCHEBI:65632
ChEBI Namecimifoetiside A
Stars
DefinitionA 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.
Last Modified20 January 2014
DownloadsMolfile
FormulaC41H66O14
Net Charge0
Average Mass782.965
Monoisotopic Mass782.44526
SMILES[H][C@@]1(O[C@H]2[C@H](O)CO[C@@]([H])(O[C@H]3CC[C@]45C[C@]46CC[C@]4(C)[C@@]7([H])[C@H](C)C[C@@]8([H])O[C@@]7(O[C@@H]8C(C)(C)O)[C@H](O)[C@@]4(C)[C@]6([H])CC[C@@]5([H])C3(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=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
InChIKeyLANJQSWIMVURCX-CXSVBUCUSA-N
Species of MetaboliteComponentSourceComments
Cimicifuga foetida (ncbitaxon:64032) aerial part (BTO:0001658) PubMed (19280146)
Roles Classification
Biological Roles:
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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-xylopyranosideChEBI
Citations