Natural Product (NP) Details

General Information of the NP (ID: NP7303)
Name
Silymarin
Synonyms
Milk thistle extract; Sabal serrulata extract; 84604-20-6; AN-35849; FT-0656490; A835184; (2S)-3,5,7-trihydroxy-2-[(2S,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one; (2S)-3,5,7-trihydroxy-2-[(2S,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
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Species Origin Carduus marianus ...     Click to Show/Hide
Carduus marianus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Silybum
Species: Carduus marianus
Disease Colorectal cancer [ICD-11: 2B91] Phase 4 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.419
 
MDCK Permeability
 -4.835
 
PAMPA
 -
 
HIA
 - - -
 
Distribution
VDss
 0.109
 
PPB
 95.3%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +
HLM Stability
 - - -
 
Excretion
CLplasma
 6.225
 
T1/2
 1.878
Toxicity
DILI
 -
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 -
 
Respiratory
 -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 ++
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C25H22O10
PubChem CID
5213
Canonical SMILES
COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
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
InChIKey
SEBFKMXJBCUCAI-UHFFFAOYSA-N
CAS Number
CAS 65666-07-1
Herb ID
HBIN044040
SymMap ID
SMIT18310
TTD Drug ID
D0AZ8C
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combined applications of doxorubicin and silymarin caused higher apoptosis and necrosis of cells in 24 h than that of single agent applications.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Silymarin possess protective effects against cisplatin hepatotoxic action in animal models.
Target and Pathway
Target(s) Arachidonate 5-lipoxygenase (5-LOX)  Molecule Info  [4]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Resolvin D biosynthesis
3 Leukotriene biosynthesis
4 Lipoxin biosynthesis
5 Aspirin triggered resolvin D biosynthesis
6 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 Serotonergic synapse
4 Ovarian steroidogenesis
5 Toxoplasmosis
NetPath Pathway IL4 Signaling Pathway Click to Show/Hide
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
WikiPathways Vitamin D Receptor Pathway Click to Show/Hide
2 Arachidonic acid metabolism
3 Eicosanoid Synthesis
4 Selenium Micronutrient Network
References
Reference 1 ClinicalTrials.gov (NCT03130634) The Efficacy of Silymarin as Adjuvant Therapy on Colorectal Cancer Patients Undergoing FOLFIRI Treatment
Reference 2 Genotoxic and cytotoxic effects of doxorubicin and silymarin on human hepatocellular carcinoma cells. Hum Exp Toxicol. 2014 Dec;33(12):1269-76.
Reference 3 Silymarin ameliorates cisplatin-induced hepatotoxicity in rats: histopathological and ultrastructural studies. Pak J Biol Sci. 2010 May 15;13(10):463-79.
Reference 4 Anti-inflammatory and anti-arthritic activities of silymarin acting through inhibition of 5-lipoxygenase. Phytomedicine. 2000 Mar;7(1):21-4.
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