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CHEBI:65903 - fomitoside E

ChEBI IDCHEBI:65903
ChEBI Namefomitoside E
Stars
DefinitionA triterpene glycoside that consists of lanost-8,23-dien-21-oic acid substituted at by a α-acetyloxy group at position 3, a hydroxy group at position 25 and a β-D-xylopyranosyl moiety at position 21 via a glycosidic linkage. Isolated from the fruit body of Fomitopsis pinicola, it exhibits inhibitory activity against COX-1 and COX-2.
Last Modified20 January 2014
DownloadsMolfile
FormulaC37H58O9
Net Charge0
Average Mass646.862
Monoisotopic Mass646.40808
SMILES[H][C@@]12CCC3=C(CC[C@@]4(C)[C@@]3(C)CC[C@]4([H])[C@@H](C/C=C/C(C)(C)O)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/C37H58O9/c1-21(38)45-28-15-17-35(6)24-14-19-36(7)23(13-18-37(36,8)25(24)11-12-27(35)34(28,4)5)22(10-9-16-33(2,3)43)31(42)46-32-30(41)29(40)26(39)20-44-32/h9,16,22-23,26-30,32,39-41,43H,10-15,17-20H2,1-8H3/b16-9+/t22-,23-,26-,27+,28-,29+,30-,32+,35-,36-,37+/m1/s1
InChIKeySZJHDEBBAHZWAS-JYUDEBFNSA-N
Species of MetaboliteComponentSourceComments
Fomitopsis pinicola (ncbitaxon:40483) fruit body (BTO:0000487) PubMed (15679320)
Roles Classification
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
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.
ChEBI Ontology
Outgoing Relation(s)
fomitoside E (CHEBI:65903) has parent hydride lanostane (CHEBI:20265)
fomitoside E (CHEBI:65903) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
fomitoside E (CHEBI:65903) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
fomitoside E (CHEBI:65903) has role fungal metabolite (CHEBI:76946)
fomitoside E (CHEBI:65903) is a acetate ester (CHEBI:47622)
fomitoside E (CHEBI:65903) is a secondary alcohol (CHEBI:35681)
fomitoside E (CHEBI:65903) is a tetracyclic triterpenoid (CHEBI:26893)
fomitoside E (CHEBI:65903) is a triterpenoid saponin (CHEBI:61778)
fomitoside E (CHEBI:65903) is a β-D-xyloside (CHEBI:27926)
IUPAC Name 
1-O-[(3α,23E)-3-acetoxy-25-hydroxy-21-oxolanosta-8,23-dien-21-yl]-β-D-xylopyranose
Synonym  Source
25-hydroxy-3α-acetoxylanost-8,23-dien-21-oicacid 21-O-β-D-xylopyranosideChEBI
Registry NumbersSources
Reaxys:10231343Reaxys
Citations