CHEBI:140078 - eruberin A

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ChEBI Name eruberin A
ChEBI ID CHEBI:140078
Definition An organic heterotetracyclic compound resulting from cyclocondensation of the 4- and 5-hydroxy groups of (2R,4S)-2-(4-methoxyphenyl)-6,8-dimethyl-3,4-dihydro-2H-chromene-4,5,7-triol across the 1- and 2-positions of β-D-glucopyranose. It is a natural product extracted from the fern plant, Pronephrium penangianum and exerts antiproliferative and antifibrotic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H28O9
Net Charge 0
Average Mass 460.479
Monoisotopic Mass 460.17333
InChI InChI=1S/C24H28O9/c1-10-18(26)11(2)22-17-15(31-23-20(28)19(27)16(9-25)32-24(23)33-22)8-14(30-21(10)17)12-4-6-13(29-3)7-5-12/h4-7,14-16,19-20,23-28H,8-9H2,1-3H3/t14-,15+,16-,19-,20+,23-,24+/m1/s1
InChIKey BVWNFYIRLQDZHV-WIGWAHHJSA-N
SMILES COC1=CC=C(C=C1)[C@H]1C[C@@H]2O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3OC3=C(C)C(O)=C(C)C(O1)=C23
Metabolite of Species Details
Abacopteris penangiana (IPNI:1136121-2) Found in aerial part (BTO:0001658). See: DOI
Pronephrium penangianum (NCBI:txid1132560) Found in whole plant (BTO:0001461). See: PubMed
Glaphyropteridopsis erubescens (NCBI:txid173878) See: DOI
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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 eruberin A (CHEBI:140078) has functional parent β-D-glucose (CHEBI:15903)
eruberin A (CHEBI:140078) has role antioxidant (CHEBI:22586)
eruberin A (CHEBI:140078) has role plant metabolite (CHEBI:76924)
eruberin A (CHEBI:140078) is a hydroxyflavan (CHEBI:72010)
eruberin A (CHEBI:140078) is a methoxybenzenes (CHEBI:51683)
eruberin A (CHEBI:140078) is a monosaccharide derivative (CHEBI:63367)
eruberin A (CHEBI:140078) is a organic heterotetracyclic compound (CHEBI:38163)
eruberin A (CHEBI:140078) is a polycyclic ether (CHEBI:36468)
IUPAC Name
(2R,7aS,9R,10S,11S,11aR,12aS)-9-(hydroxymethyl)-2-(4-methoxyphenyl)-4,6-dimethyl-1,9,10,11,11a,12a-hexahydro-2H,7aH-pyrano[2',3':2,3][1,4]dioxepino[5,6,7-de]chromene-5,10,11-triol
Synonym Source
1,2-O-[3,4-dihydro-7-hydroxy-2-(4-methoxyphenyl)-6,8-dimethyl-2H-1-benzopyran-5,4-diyl]-β-D-glucopyranose ChEBI
Manual Xrefs Databases
10270537 ChemSpider
C00008978 KNApSAcK
LMPK12020167 LIPID MAPS
US20140348965 Patent
View more database links
Registry Number Type Source
90146-68-2 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
26279445 PubMed citation Europe PMC
28210075 PubMed citation Europe PMC
31950023 PubMed citation Europe PMC
32140388 PubMed citation Europe PMC
Last Modified
25 October 2021
General Comment
2021-10-25 Conflicting data on absolute configuration. Later isolates compared with Eruberin A shown as having (2S,4R)-stereochemistry, but the original paper give Eruberin A as (2R,4S)-stereochemistry as illustrated.