CHEBI:66674 - marianoside A

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ChEBI Name marianoside A
ChEBI ID CHEBI:66674
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C37H62O8
Net Charge 0
Average Mass 634.88340
Monoisotopic Mass 634.44447
InChI InChI=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
InChIKey BQSKVEDRDUPKAI-ADEYTEBPSA-N
SMILES [H][C@@]1(CC[C@]2(C)C3=C(CC[C@@]2([H])[C@]1(C)CO)[C@]1(C)CC[C@]([H])([C@H](C)CCC(=C)C(C)(C)O)[C@@]1(C)CC3)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Silybum marianum (NCBI:txid92921) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): 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.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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-glucopyranoside ChEBI
Citation Waiting for Citations Type Source
16394559 PubMed citation Europe PMC
Last Modified
20 January 2014