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CHEBI:28332 - scilliroside

ChEBI IDCHEBI:28332
ChEBI Namescilliroside
Stars
DefinitionA β-D-glucoside that is scillirosidin in which the hydroxy group at position 3 is substituted by a β-D-glucopyranoside group. It is a rodenticide extracted from the bulb of the Mediterranean squill plant and was used for the control of Norway rats, black rats, house mice, long-tailed field mice, and field voles.
Secondary ChEBI IDsCHEBI:9052, CHEBI:26609
Last Modified14 January 2021
DownloadsMolfile
FormulaC32H44O12
Net Charge0
Average Mass620.692
Monoisotopic Mass620.28328
SMILES[H][C@]12CC[C@@]3(C)[C@](O)(CC[C@]3([H])c3ccc(=O)oc3)[C@]1(O)C[C@@H](OC(C)=O)C1=C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@@]12C
InChIInChI=1S/C32H44O12/c1-16(34)42-21-13-31(39)23(8-10-30(3)19(7-11-32(30,31)40)17-4-5-24(35)41-15-17)29(2)9-6-18(12-20(21)29)43-28-27(38)26(37)25(36)22(14-33)44-28/h4-5,12,15,18-19,21-23,25-28,33,36-40H,6-11,13-14H2,1-3H3/t18-,19+,21+,22+,23+,25+,26-,27+,28+,29-,30+,31-,32+/m0/s1
InChIKeyLSMIOFMZNVEEBR-ICLSSMQGSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Drimia maritima (ncbitaxon:82070) bulb (BTO:0000159) PubMed (17236017)
Urginea pancration (IPNI:543298-1) bulb (BTO:0000159) PubMed (17221395)
Roles Classification
Biological Role:
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor  An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
Application:
rodenticide  A substance used to destroy rodent pests.
ChEBI Ontology
Outgoing Relation(s)
scilliroside (CHEBI:28332) has functional parent scillirosidin (CHEBI:37417)
scilliroside (CHEBI:28332) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
scilliroside (CHEBI:28332) has role rodenticide (CHEBI:33288)
scilliroside (CHEBI:28332) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
6β-(acetyloxy)-3β-(β-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
Synonyms  Source
scillirosideKEGG COMPOUND
scillirosidin 3-O-β-D-glucosideKEGG COMPOUND
3β-(β-D-glucopyranosyloxy)-17β-(2-oxo-2H-pyran-5-yl)-14β-androst-4-ene-6β,8,14-triol 6-acetateAlan Wood's Pesticides
(3β,6β)-6-(acetyloxy)-3-(β-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolideAlan Wood's Pesticides
3-O-(β-D-glucopyranosyl)-6β-acetoxy-3β,8β,14β-trihydroxybufa-4,20,22-trienolideLIPID MAPS
scillirosidin 3-O-glucosideLIPID MAPS
Brand Names  Source
Red squillChemIDplus
SilmineChemIDplus
DethdietChEBI
RodineChEBI
RodeneChEBI
SilmurinChemIDplus
Manual XrefsDatabases
C08880KEGG COMPOUND
C00003637KNApSAcK
LMST01130007LIPID MAPS
scillirosideAlan Wood's Pesticides
ScillirosideWikipedia
390447ChemSpider
588BPDB
CH634200Patent
Registry NumbersSources
Reaxys:74900Reaxys
CAS:507-60-8KEGG COMPOUND
CAS:507-60-8ChemIDplus
Citations