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CHEBI:66278 - tsugarioside C

ChEBI IDCHEBI:66278
ChEBI Nametsugarioside C
Stars
DefinitionA triterpenoid saponin that is (23Z)-24-methyllanosta-8,23,25-trien-21-oic acid substituted by an acetyloxy group at position 3 and a β-D-xylopyranosyl residue at position 21 via a glycosidic linkage. It has been isolated from the fruit bodied of Ganoderma tsugae and exhibits cytotoxic activity against several different cancer cell lines.
Last Modified27 November 2014
DownloadsMolfile
FormulaC38H58O8
Net Charge0
Average Mass642.874
Monoisotopic Mass642.41317
SMILES[H][C@@]12CCC3=C(CC[C@@]4(C)[C@@]3(C)CC[C@]4([H])[C@@H](C/C=C(/C)C(=C)C)C(=O)O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@@]1(C)CC[C@@H](OC(C)=O)C2(C)C
InChIInChI=1S/C38H58O8/c1-21(2)22(3)10-11-24(33(43)46-34-32(42)31(41)28(40)20-44-34)25-14-18-38(9)27-12-13-29-35(5,6)30(45-23(4)39)16-17-36(29,7)26(27)15-19-37(25,38)8/h10,24-25,28-32,34,40-42H,1,11-20H2,2-9H3/b22-10-/t24-,25-,28-,29+,30-,31+,32-,34+,36-,37-,38+/m1/s1
InChIKeyRJBCIJBIKBHZMX-MGAAYXLPSA-N
Species of MetaboliteComponentSourceComments
Ganoderma tsugae (ncbitaxon:34467) fruit body (BTO:0000487) PubMed (10785428)
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
tsugarioside C (CHEBI:66278) has parent hydride lanostane (CHEBI:20265)
tsugarioside C (CHEBI:66278) has role antineoplastic agent (CHEBI:35610)
tsugarioside C (CHEBI:66278) has role fungal metabolite (CHEBI:76946)
tsugarioside C (CHEBI:66278) is a acetate ester (CHEBI:47622)
tsugarioside C (CHEBI:66278) is a monosaccharide derivative (CHEBI:63367)
tsugarioside C (CHEBI:66278) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
1-O-[(3α,23Z)-3-(acetyloxy)-24-methyl-21-oxolanosta-8,23,25-trien-21-yl]-β-D-xylopyranose
Manual XrefsDatabases
C00047114KNApSAcK
Registry NumbersSources
Reaxys:8605255Reaxys
Citations