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CHEBI:140715 - clarinoside

ChEBI IDCHEBI:140715
ChEBI Nameclarinoside
Stars
DefinitionA naphthopyran that is 1H-naphtho[2,3-c]pyran-5,10-diol in which the hydroxy group at position 5 (furthest from the pyran oxygen) has been converted to the corresponding β-D-glucoside, while that at position 10 has been converted to the corresponding 6-deoxy-β-D-glucopyranoside (β-D-quinovoside). It was isolated from the flowered aerial parts of the annual plant Mitracarpus scaber.
Last Modified20 September 2018
SubmitterGrégory Genta-Jouve
DownloadsMolfile
FormulaC25H30O12
Net Charge0
Average Mass522.503
Monoisotopic Mass522.17373
SMILESC[C@H]1O[C@@H](Oc2c3c(c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c4ccccc24)C=COC3)[C@H](O)[C@@H](O)[C@@H]1O
InChIInChI=1S/C25H30O12/c1-10-16(27)18(29)20(31)24(34-10)37-23-12-5-3-2-4-11(12)22(13-6-7-33-9-14(13)23)36-25-21(32)19(30)17(28)15(8-26)35-25/h2-7,10,15-21,24-32H,8-9H2,1H3/t10-,15-,16-,17-,18+,19+,20-,21-,24+,25+/m1/s1
InChIKeyJRJWTHQYOKFMNP-BSKDJEKXSA-N
Species of MetaboliteComponentSourceComments
Mitracarpus scaber (IPNI:756246-1) aerial part (BTO:0001658) Article (Molecules, 2018, 23, 1237)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
clarinoside (CHEBI:140715) has role anti-inflammatory agent (CHEBI:67079)
clarinoside (CHEBI:140715) has role plant metabolite (CHEBI:76924)
clarinoside (CHEBI:140715) is a naphthopyran (CHEBI:86027)
clarinoside (CHEBI:140715) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
5-(β-D-glucopyranosyloxy)-1H-naphtho[2,3-c]pyran-10-yl 6-deoxy-β-D-glucopyranoside
Synonyms  Source
5,10-dihydroxy-2H-naphtho[2,3-b]pyran-5-β-D-glucopyranosyl-10-β-D-quinovopyranosideChEBI
5-(β-D-glucopyranosyloxy)-1H-naphtho[2,3-c]pyran-10-yl β-D-quinovopyranosideChEBI
Registry NumbersSources
Reaxys:32869939Reaxys
Citations