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CHEBI:66575 - leufolin A

ChEBI IDCHEBI:66575
ChEBI Nameleufolin A
Stars
DefinitionA 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.
Last Modified9 April 2018
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)c4c(O)cc(O)cc4O3)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)39-14-24-27(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
InChIKeyLBJRQQUCMONTPV-AVNPKAOGSA-N
Species of MetaboliteComponentSourceComments
Leucas urticifolia (ncbitaxon:483843) whole plant (BTO:0001461) PubMed (17909500)
Roles Classification
Biological Roles:
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).
ChEBI Ontology
Outgoing Relation(s)
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 (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)
leufolin A (CHEBI:66575) is a β-D-glucoside (CHEBI:22798)
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-propenoateChEBI
Registry NumbersSources
Reaxys:11126779Reaxys
Citations