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CHEBI:66674 - marianoside A

ChEBI IDCHEBI:66674
ChEBI Namemarianoside A
Stars
DefinitionA triterpene glycoside that is lanost-8-ene substituted by hydroxy groups at positions 25 and 28, a methylidene group at position 24 and a β-D-glucopyranosyloxy group at position 3. Isolated from the whole plant of Silybum marianum, it exhibits inhibitory activity against chymotrypsin.
Last Modified20 January 2014
DownloadsMolfile
FormulaC37H62O8
Net Charge0
Average Mass634.895
Monoisotopic Mass634.44447
SMILES[H][C@@]12CCC3=C(CC[C@@]4(C)[C@@]3(C)CC[C@]4([H])[C@H](C)CCC(=C)C(C)(C)O)[C@@]1(C)CC[C@]([H])(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@]2(C)CO
InChIInChI=1S/C37H62O8/c1-21(9-10-22(2)33(3,4)43)23-13-17-37(8)25-11-12-27-34(5,24(25)14-18-36(23,37)7)16-15-28(35(27,6)20-39)45-32-31(42)30(41)29(40)26(19-38)44-32/h21,23,26-32,38-43H,2,9-20H2,1,3-8H3/t21-,23-,26-,27-,28+,29-,30+,31-,32+,34-,35+,36-,37+/m1/s1
InChIKeyBQSKVEDRDUPKAI-ADEYTEBPSA-N
Species of MetaboliteComponentSourceComments
Silybum marianum (ncbitaxon:92921) whole plant (BTO:0001461) PubMed (16394559)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.4.21.1 (chymotrypsin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of chymotrypsin (EC 3.4.21.1).
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)
marianoside A (CHEBI:66674) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
marianoside A (CHEBI:66674) has role plant metabolite (CHEBI:76924)
marianoside A (CHEBI:66674) is a primary alcohol (CHEBI:15734)
marianoside A (CHEBI:66674) is a tertiary alcohol (CHEBI:26878)
marianoside A (CHEBI:66674) is a tetracyclic triterpenoid (CHEBI:26893)
marianoside A (CHEBI:66674) is a triterpenoid saponin (CHEBI:61778)
marianoside A (CHEBI:66674) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3β)-25,28-dihydroxy-24-methylidenelanost-8-en-3-yl β-D-glucopyranoside
Synonym  Source
24-methylene-lanoesta-8(9)-ene-25,28-diol 3-O-β-D-glucopyranosideChEBI
Citations