Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1913)
Drug Name
Silymarin
Synonyms
Sabal serrulata extract; Milk thistle extract; (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; (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; 84604-20-6; A835184; AN-35849; FT-0656490
Indication Fatty liver disease [ICD11: DB92] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 482.4 Topological Polar Surface Area 155
Heavy Atom Count 35 Rotatable Bond Count 4
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
44147684
PubChem SID
126683925 ; 131322744 ; 164830271 ; 223682946
CAS Number
22888-70-6
TTD Drug ID
D0AZ8C
Formula
C25H22O10
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/t20-,23?,24+,25-/m0/s1
InChIKey
SEBFKMXJBCUCAI-VGHNRKBZSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
20-O-beta-D-Glu DM004883 N. A. Conjugation - Glucuronidation 1 [3] , [4]
O-demethylated-silybin DM004882
78210148
Oxidation - O-dealkylation 1 [5] , [4]
Silybin 7-glucoside DM004884
11093488
Conjugation - Glucuronidation 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005261 Silymarin O-demethylated-silybin Oxidation - O-dealkylation CYP2C8 [5], [4]
MR005262 Silymarin 20-O-beta-D-Glu Conjugation - Glucuronidation UGT1A1 ... [3], [4]
MR005263 Silymarin Silybin 7-glucoside Conjugation - Glucuronidation UGT1A1 ... [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[3] , [4]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[3] , [4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3] , [4]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[3] , [4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3] , [4]
⏷ Show the Full List of 6  DME(s)
References
1 ClinicalTrials.gov (NCT02973295) Silymarin in NAFLD.
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 Evidence for differences in regioselective and stereoselective glucuronidation of silybin diastereomers from milk thistle (Silybum marianum) by human UDP-glucuronosyltransferases
4 Metabolism, Transport and Drug-Drug Interactions of Silymarin
5 Application of liquid chromatography-electrospray ionization-ion trap mass spectrometry to investigate the metabolism of silibinin in human liver microsomes

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