CHEBI:66675 - marianoside B

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ChEBI Name marianoside B
ChEBI ID CHEBI:66675
Definition A triterpene glycoside that is lanost-8-ene substituted by 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 C37H62O6
Net Charge 0
Average Mass 602.88460
Monoisotopic Mass 602.45464
InChI InChI=1S/C37H62O6/c1-21(2)22(3)10-11-23(4)24-14-18-37(9)26-12-13-28-34(5,6)29(16-17-35(28,7)25(26)15-19-36(24,37)8)43-33-32(41)31(40)30(39)27(20-38)42-33/h21,23-24,27-33,38-41H,3,10-20H2,1-2,4-9H3/t23-,24-,27-,28+,29+,30-,31+,32-,33+,35-,36-,37+/m1/s1
InChIKey PHOVCZWDVRTEJJ-SAMWAVPASA-N
SMILES [H][C@@]1(CC[C@]2(C)C3=C(CC[C@@]2([H])C1(C)C)[C@]1(C)CC[C@]([H])([C@H](C)CCC(=C)C(C)C)[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): 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).
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.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing marianoside B (CHEBI:66675) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
marianoside B (CHEBI:66675) has role plant metabolite (CHEBI:76924)
marianoside B (CHEBI:66675) is a β-D-glucoside (CHEBI:22798)
marianoside B (CHEBI:66675) is a tetracyclic triterpenoid (CHEBI:26893)
marianoside B (CHEBI:66675) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β)-24-methylidenelanost-8-en-3-yl β-D-glucopyranoside
Synonym Source
24-methylene-lanoesta-8(9)-ene 3-O-β-D-glucopyranoside ChEBI
Manual Xref Database
9846362 ChemSpider
View more database links
Registry Number Type Source
10321312 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16394559 PubMed citation Europe PMC
Last Modified
20 January 2014