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
ATC Code
A05BA03: Silymarin
A05BA: Liver therapy
A05B: LIVER THERAPY, LIPOTROPICS
A05: BILE AND LIVER THERAPY
A: ALIMENTARY TRACT AND METABOLISM
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
CHEMBL125451
CAS Number
65666-07-1
TTD ID
D0AZ8C
VARIDT ID
DR01185
INTEDE ID
DR1913
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]
Cyclin-A1 (CCNA1) OTX4HD45 CCNA1_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [5]
G1/S-specific cyclin-D3 (CCND3) OTNKPQ22 CCND3_HUMAN Gene/Protein Processing [5]
M-phase inducer phosphatase 1 (CDC25A) OTSLKKCO MPIP1_HUMAN Gene/Protein Processing [5]
M-phase inducer phosphatase 2 (CDC25B) OT12MSRY MPIP2_HUMAN Gene/Protein Processing [5]
M-phase inducer phosphatase 3 (CDC25C) OTPQI71S MPIP3_HUMAN Gene/Protein Processing [5]
Methylated-DNA--protein-cysteine methyltransferase (MGMT) OT40A9WH MGMT_HUMAN Gene/Protein Processing [6]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [7]
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 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.
6 Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. Carcinogenesis. 2007 Feb;28(2):378-89.
7 Stable cellular models of nuclear receptor PXR for high-throughput evaluation of small molecules. Toxicol In Vitro. 2018 Oct;52:222-234.