CHEBI:66575 - leufolin A

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ChEBI Name leufolin A
ChEBI ID CHEBI:66575
Definition A flavanone glycoside that is (S)-naringenin 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)39-14-24-27(36)28(37)29(38)30(42-24)40-19-8-4-16(5-9-19)22-13-21(34)26-20(33)11-18(32)12-23(26)41-22/h1-12,22,24,27-33,36-38H,13-14H2/b10-3+/t22-,24+,27+,28-,29+,30+/m0/s1
InChIKey LBJRQQUCMONTPV-AVNPKAOGSA-N
SMILES O[C@@H]1[C@@H](COC(=O)\C=C\c2ccc(O)cc2)O[C@@H](Oc2ccc(cc2)[C@@H]2CC(=O)c3c(O)cc(O)cc3O2)[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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing leufolin A (CHEBI:66575) has functional parent (S)-naringenin (CHEBI:17846)
leufolin A (CHEBI:66575) has functional parent trans-4-coumaric acid (CHEBI:32374)
leufolin A (CHEBI:66575) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
leufolin A (CHEBI:66575) has role metabolite (CHEBI:25212)
leufolin A (CHEBI:66575) is a β-D-glucoside (CHEBI:22798)
leufolin A (CHEBI:66575) is a (2S)-flavan-4-one (CHEBI:140377)
leufolin A (CHEBI:66575) is a cinnamate ester (CHEBI:36087)
leufolin A (CHEBI:66575) is a dihydroxyflavanone (CHEBI:38749)
leufolin A (CHEBI:66575) is a flavanone glycoside (CHEBI:72730)
IUPAC Name
4-[(2S)-5,7-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-(5,7-dihydroxy-4-oxo-3,4-dihydro-H-chromen-2-yl)phenoxy]-3,4,5-trihydroxytetrahydro-2H-pyran- 2-yl}methyl-(E)-3-(4-hydroxyphenyl)-2-propenoate ChEBI
Registry Number Type Source
11126779 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17909500 PubMed citation Europe PMC
Last Modified
09 April 2018