CHEBI:66576 - leufolin B

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ChEBI Name leufolin B
ChEBI ID CHEBI:66576
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H28O12
Net Charge 0
Average Mass 580.53610
Monoisotopic Mass 580.15808
InChI InChI=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
InChIKey QVEGPDNSRBIZKA-QXAKUUBASA-N
SMILES O[C@@H]1[C@@H](COC(=O)\C=C\c2ccc(O)cc2)O[C@@H](Oc2ccc(cc2)[C@@H]2CC(=O)c3cc(O)cc(O)c3O2)[C@H](O)[C@H]1O
Metabolite of Species Details
Leucas urticifolia (NCBI:txid483843) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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-propenoate ChEBI
Registry Number Type Source
11126780 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17909500 PubMed citation Europe PMC
Last Modified
22 March 2013