CHEBI:140715 - clarinoside

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ChEBI Name clarinoside
ChEBI ID CHEBI:140715
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Grégory Genta-Jouve
Supplier Information
Download Molfile XML SDF
Formula C25H30O12
Net Charge 0
Average Mass 522.499
Monoisotopic Mass 522.17373
InChI InChI=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
InChIKey JRJWTHQYOKFMNP-BSKDJEKXSA-N
SMILES C=1C=2C(C=CC1)=C(C3=C(C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C)O)O)O)COC=C3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Metabolite of Species Details
Mitracarpus scaber (IPNI:756246-1) Found in aerial part (BTO:0001658). See: Molecules, 2018, 23, 1237
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.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing clarinoside (CHEBI:140715) has role anti-inflammatory agent (CHEBI:67079)
clarinoside (CHEBI:140715) has role plant metabolite (CHEBI:76924)
clarinoside (CHEBI:140715) is a β-D-glucoside (CHEBI:22798)
clarinoside (CHEBI:140715) is a naphthopyran (CHEBI:86027)
IUPAC Name
5-(β-D-glucopyranosyloxy)-1H-naphtho[2,3-c]pyran-10-yl 6-deoxy-β-D-glucopyranoside
Synonyms Sources
5,10-dihydroxy-2H-naphtho[2,3-b]pyran-5-β-D-glucopyranosyl-10-β-D-quinovopyranoside ChEBI
5-(β-D-glucopyranosyloxy)-1H-naphtho[2,3-c]pyran-10-yl β-D-quinovopyranoside ChEBI
Registry Number Type Source
32869939 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
29789477 PubMed citation Europe PMC
Last Modified
20 September 2018