CHEBI:9138 - silandrin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name silandrin
ChEBI ID CHEBI:9138
Definition A flavonolignan isolated from milk thistle, Silybum marianum, and has been shown to exhibit hepatoprotective activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB3167375, ChemicalBook:CB4183426, eMolecules:494487, ZINC000000899824
Download Molfile XML SDF
Formula C25H22O9
Net Charge 0
Average Mass 466.43680
Monoisotopic Mass 466.12638
InChI InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3/t19-,23+,25+/m0/s1
InChIKey CRPGUMMYQABYES-DNVKUUNQSA-N
SMILES [H][C@]1(CC(=O)c2c(O)cc(O)cc2O1)c1ccc2O[C@@]([H])([C@@H](CO)Oc2c1)c1ccc(O)c(OC)c1
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing silandrin (CHEBI:9138) has role hepatoprotective agent (CHEBI:62868)
silandrin (CHEBI:9138) has role metabolite (CHEBI:25212)
silandrin (CHEBI:9138) is a aromatic ether (CHEBI:35618)
silandrin (CHEBI:9138) is a benzodioxine (CHEBI:64096)
silandrin (CHEBI:9138) is a flavonolignan (CHEBI:72709)
silandrin (CHEBI:9138) is a polyphenol (CHEBI:26195)
IUPAC Name
(2S)-5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
Synonym Source
(−)-silandrin ChEBI
Manual Xrefs Databases
C00001002 KNApSAcK
C08600 KEGG COMPOUND
HMDB0033325 HMDB
LMPK12140414 LIPID MAPS
View more database links
Registry Numbers Types Sources
4772951 Reaxys Registry Number Reaxys
70815-32-6 CAS Registry Number KEGG COMPOUND
Citations Types Sources
17402024 PubMed citation Europe PMC
18366865 PubMed citation Europe PMC
Last Modified
28 July 2014