Details of the Drug

General Information of Drug (ID: DMXBYQR)

Drug 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
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 482.4
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C25H22O10
IUPAC Name
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
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
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
Cross-matching ID
PubChem CID
5213
ChEBI ID
CHEBI:125451
CAS Number
65666-07-1
TTD ID
D0AZ8C
VARIDT ID
DR01185
INTEDE ID
DR1913

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)
Main DME 		DEYGVN4 UD11_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [3]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [4]
Catalase (CAT) OTHEBX9R CATA_HUMAN Gene/Protein Processing [5]
Cyclin-A1 (CCNA1) OTX4HD45 CCNA1_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase 1 (CDK1) OTW1SC2N CDK1_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase 2 (CDK2) OTB5DYYZ CDK2_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase 4 (CDK4) OT7EP05T CDK4_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [6]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [6]
G1/S-specific cyclin-D3 (CCND3) OTNKPQ22 CCND3_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Arachidonate 5-lipoxygenase (5-LOX) DTT ALOX5 7.42E-01 -0.18 -0.25
Arachidonate 5-lipoxygenase (5-LOX) DTT ALOX5 1.25E-03 0.43 0.63
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 8.29E-01 -5.44E-03 -2.25E-02
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 4.23E-03 9.31E-02 4.30E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Anti-inflammatory and anti-arthritic activities of silymarin acting through inhibition of 5-lipoxygenase. Phytomedicine. 2000 Mar;7(1):21-4.
2 Role of UDP-glucuronosyltransferase 1A1 in the metabolism and pharmacokinetics of silymarin flavonolignans in patients with HCV and NAFLD. Molecules. 2017 Jan 15;22(1). pii: E142.
3 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
4 Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate. Toxicol Sci. 2007 Apr;96(2):227-36. doi: 10.1093/toxsci/kfl147. Epub 2006 Oct 31.
5 Silymarin protects PBMC against B(a)P induced toxicity by replenishing redox status and modulating glutathione metabolizing enzymes--an in vitro study. Toxicol Appl Pharmacol. 2010 Sep 1;247(2):116-28.
6 Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells. Int J Cancer. 2008 Jul 1;123(1):41-50. doi: 10.1002/ijc.23485.