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CHEBI:140078 - eruberin A

ChEBI IDCHEBI:140078
ChEBI Nameeruberin A
Stars
DefinitionAn 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.
Last Modified3 February 2025
Submittermwilliams
DownloadsMolfile
FormulaC24H28O9
Net Charge0
Average Mass460.479
Monoisotopic Mass460.17333
SMILESCOc1ccc([C@H]2C[C@@H]3O[C@H]4[C@H](Oc5c(C)c(O)c(C)c(c53)O2)O[C@H](CO)[C@@H](O)[C@@H]4O)cc1
InChIInChI=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
InChIKeyBVWNFYIRLQDZHV-WIGWAHHJSA-N
Species of MetaboliteComponentSourceComments
Pronephrium penangianum (ncbitaxon:1132560) whole plant (BTO:0001461) PubMed (26279445)
Glaphyropteridopsis erubescens (ncbitaxon:173878) - DOI (10.1248/cpb.32.490)
Abacopteris penangiana (IPNI:1136121-2) aerial part (BTO:0001658) DOI (10.1021/np0703850)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antifibrotic agent  Any agent which acts to reduce fibrosis.
ChEBI Ontology
Outgoing Relation(s)
eruberin A (CHEBI:140078) has functional parent β-D-glucose (CHEBI:15903)
eruberin A (CHEBI:140078) has role antifibrotic agent (CHEBI:233423)
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-glucopyranoseChEBI
Manual XrefsDatabases
LMPK12020167LIPID MAPS
C00008978KNApSAcK
US20140348965Patent
10270537ChemSpider
Registry NumbersSources
CAS:90146-68-2KNApSAcK
Citations