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> Main
CHEBI:9144 - silibinin
Main
ChEBI Ontology
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ChEBI Name
silibinin
ChEBI ID
CHEBI:9144
Definition
A flavonolignan isolated from milk thistle,
Silybum marianum
, that has been shown to exhibit antioxidant and antineoplastic activities.
Stars
This entity has been manually annotated by the ChEBI Team.
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Wikipedia
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Read full article at Wikipedia
Formula
C25H22O10
Net Charge
0
Average Mass
482.43620
Monoisotopic Mass
482.12130
InChI
InChI=1S/C25H22O10/c1-
32-
17-
6-
11(2-
4-
14(17)
28)
24-
20(10-
26)
33-
16-
5-
3-
12(7-
18(16)
34-
24)
25-
23(31)
22(30)
21-
15(29)
8-
13(27)
9-
19(21)
35-
25/h2-
9,20,23-
29,31H,10H2,1H3/t20-
,23+,24-
,25-
/m1/s1
InChIKey
SEBFKMXJBCUCAI-HKTJVKLFSA-N
SMILES
[H][C@@]1(Oc2cc(ccc2O[C@@H]1CO)[C@@]1([H])Oc2cc(O)cc(O)c2C(=O)[C@@H]1O)c1ccc(O)c(OC)c1
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.
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
silibinin (
CHEBI:9144
)
has role
antineoplastic agent (
CHEBI:35610
)
silibinin (
CHEBI:9144
)
has role
antioxidant (
CHEBI:22586
)
silibinin (
CHEBI:9144
)
has role
hepatoprotective agent (
CHEBI:62868
)
silibinin (
CHEBI:9144
)
has role
plant metabolite (
CHEBI:76924
)
silibinin (
CHEBI:9144
)
is a
aromatic ether (
CHEBI:35618
)
silibinin (
CHEBI:9144
)
is a
benzodioxine (
CHEBI:64096
)
silibinin (
CHEBI:9144
)
is a
flavonolignan (
CHEBI:72709
)
silibinin (
CHEBI:9144
)
is a
polyphenol (
CHEBI:26195
)
silibinin (
CHEBI:9144
)
is a
secondary α-hydroxy ketone (
CHEBI:2468
)
IUPAC Name
(2
R
,3
R
)-
3,5,7-
trihydroxy-
2-
[(2
R
,3
R
)-
3-
(4-
hydroxy-
3-
methoxyphenyl)-
2-
(hydroxymethyl)-
2,3-
dihydro-
1,4-
benzodioxin-
6-
yl]-
2,3-
dihydro-
4
H
-
chromen-
4-
one
INNs
Sources
silibinin
KEGG DRUG
silibinina
WHO MedNet
silibinine
WHO MedNet
silibininum
WHO MedNet
Synonyms
Sources
Flavobin
HMDB
Karsil
HMDB
Silibinin
KEGG COMPOUND
Silibinine
HMDB
Silybin
KEGG COMPOUND
Silymarin
KEGG COMPOUND
Manual Xrefs
Databases
C00001003
KNApSAcK
C07610
KEGG COMPOUND
CN102727484
Patent
D08515
KEGG DRUG
HMDB0030583
HMDB
Silibinin
Wikipedia
View more database links
Registry Numbers
Types
Sources
1632852
Reaxys Registry Number
Reaxys
22888-70-6
CAS Registry Number
ChemIDplus
Citations
Types
Sources
22086675
PubMed citation
Europe PMC
22555054
PubMed citation
Europe PMC
22899727
PubMed citation
Europe PMC
23073223
PubMed citation
Europe PMC
23357565
PubMed citation
Europe PMC
23402882
PubMed citation
Europe PMC
Last Modified
06 February 2018