EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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

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.
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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