CHEBI:68340 - β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside

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ChEBI Name β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside
ChEBI ID CHEBI:68340
ChEBI ASCII Name beta-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[beta-D-apiofuranosyl-(1->2)]-beta-D-glucopyranoside
Definition A phenylethanoid that is the 4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranosyl derivative of 4-(2-hydroxyethyl)phenol. Isolated from Lepisorus contortus, it exhibits inhibitory activities against aromatase and NF-κB.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H34O14
Net Charge 0
Average Mass 594.56120
Monoisotopic Mass 594.19486
InChI InChI=1S/C28H34O14/c29-12-20-23(41-21(34)8-4-16-3-7-18(32)19(33)11-16)22(35)24(42-27-25(36)28(37,13-30)14-39-27)26(40-20)38-10-9-15-1-5-17(31)6-2-15/h1-8,11,20,22-27,29-33,35-37H,9-10,12-14H2/b8-4+/t20-,22+,23-,24-,25+,26-,27+,28-/m1/s1
InChIKey TXTPNFUSMTWSFE-JCJVHILYSA-N
SMILES [H][C@]1(OC[C@](O)(CO)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H](CO)O[C@H]1OCCc1ccc(O)cc1
Metabolite of Species Details
Lepisorus contortus (NCBI:txid699669) Found in whole plant (BTO:0001461). 95% EtOH extract of air-dried, powdered whole plant See: PubMed
Roles Classification
Biological Role(s): EC 1.14.14.14 (aromatase) inhibitor
An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role EC 1.14.14.14 (aromatase) inhibitor (CHEBI:50790)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role NF-κB inhibitor (CHEBI:73240)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role plant metabolite (CHEBI:76924)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a β-D-glucoside (CHEBI:22798)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a alkyl caffeate ester (CHEBI:65331)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a phenylethanoid (CHEBI:74644)
IUPAC Name
2-(4-hydroxyphenyl)ethyl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Citation Waiting for Citations Type Source
21261296 PubMed citation Europe PMC
Last Modified
25 March 2015