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

Default Structure
ChEBI IDCHEBI:68340
ChEBI Nameβ-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside
Stars
ASCII Namebeta-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[beta-D-apiofuranosyl-(1->2)]-beta-D-glucopyranoside
DefinitionA 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.
Last Modified25 March 2015
DownloadsMolfile
FormulaC28H34O14
Net Charge0
Average Mass594.566
Monoisotopic Mass594.19486
SMILES[H][C@@]1(O[C@H]2[C@H](OCCc3ccc(O)cc3)O[C@H](CO)[C@@H](OC(=O)/C=C/c3ccc(O)c(O)c3)[C@@H]2O)OC[C@](O)(CO)[C@H]1O
InChIInChI=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
InChIKeyTXTPNFUSMTWSFE-JCJVHILYSA-N
Species of MetaboliteComponentSourceComments
Lepisorus contortus (ncbitaxon:699669) whole plant (BTO:0001461) PubMed (21261296) 95% EtOH extract of air-dried, powdered whole plant
Roles Classification
Biological Roles:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
ChEBI Ontology
Outgoing Relation(s)
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 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)
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)
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
Citations