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CHEBI:66576 - leufolin B

Default Structure
ChEBI IDCHEBI:66576
ChEBI Nameleufolin B
Stars
DefinitionA flavanone glycoside that is 6,8,4'-trihydroxyflavanone attached to a 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranosyl moiety at position 4' via a glycosidic linkage. Isolated from Leucas urticifolia, it acts as a cholinesterase inhibitor.
Last Modified22 March 2013
DownloadsMolfile
FormulaC30H28O12
Net Charge0
Average Mass580.542
Monoisotopic Mass580.15808
SMILESO=C(/C=C/c1ccc(O)cc1)OC[C@H]1O[C@@H](Oc2ccc([C@@H]3CC(=O)c4cc(O)cc(O)c4O3)cc2)[C@H](O)[C@@H](O)[C@@H]1O
InChIInChI=1S/C30H28O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-26(36)27(37)28(38)30(42-24)40-19-8-4-16(5-9-19)23-13-21(33)20-11-18(32)12-22(34)29(20)41-23/h1-12,23-24,26-28,30-32,34,36-38H,13-14H2/b10-3+/t23-,24+,26+,27-,28+,30+/m0/s1
InChIKeyQVEGPDNSRBIZKA-QXAKUUBASA-N
Species of MetaboliteComponentSourceComments
Leucas urticifolia (ncbitaxon:483843) whole plant (BTO:0001461) PubMed (17909500)
Roles Classification
Biological Roles:
EC 3.1.1.8 (cholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
leufolin B (CHEBI:66576) has functional parent trans-4-coumaric acid (CHEBI:32374)
leufolin B (CHEBI:66576) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
leufolin B (CHEBI:66576) has role metabolite (CHEBI:25212)
leufolin B (CHEBI:66576) is a cinnamate ester (CHEBI:36087)
leufolin B (CHEBI:66576) is a dihydroxyflavanone (CHEBI:38749)
leufolin B (CHEBI:66576) is a flavanone glycoside (CHEBI:72730)
leufolin B (CHEBI:66576) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
4-[(2S)-6,8-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]phenyl 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Synonym  Source
{6-[4-(6,8-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,5-dihydroxytetrahydro-2Hpyran-2-yl}methyl-(E)-3(4-hydroxyphenyl)-2-propenoateChEBI
Registry NumbersSources
Reaxys:11126780Reaxys
Citations