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CHEBI:66576 - leufolin B

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:
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 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