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

General Information of Drug (ID: DR2606)
Drug Name
Liquiritin
Synonyms
Likviritin; Liquiritigenin-4'-O-glucoside; Liquiritigenin-4'-beta-glucoside; Liquiritin; Liquiritoside; T0O79T74CD; (2S)-7-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]chroman-4-one; 4',7-Dihydroxyflavanone 4'-(beta-D-glucopyranoside); 4',7-Dihydroxyflavanone 4'-(beta-D-glucoside); 4'-O-beta-D-glucopyranosyl-7-hydroxyflavan-4-one; 551-15-5; 7-Hydroxyflavanone 4'-O-glucoside; AK168177; CHEBI:80845; CHEMBL511995; DTXSID40203619; MLS000575018; UNII-T0O79T74CD
Indication Rheumatoid arthritis [ICD11: FA20] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 418.4 Topological Polar Surface Area 146
Heavy Atom Count 30 Rotatable Bond Count 4
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
503737
ChEBI ID
CHEBI:80845
CAS Number
551-15-5
Formula
C21H22O9
Canonical SMILES
C1C(OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O
InChI
1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1
InChIKey
DEMKZLAVQYISIA-ZRWXNEIDSA-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
Liquiritin metabolite M2 DM005514 N. A. Conjugation - Acetylation 1 [2]
Liquiritin metabolite M3 DM005510
1889
Oxidation - Deglycosylation 1 [2] , [3]
Liquiritin metabolite M7 DM005502
638278
Multi-steps Reaction - Ring cleavage reaction; hydrolysis 1 [3]
Liquiritin metabolite M12 DM005509 N. A. Conjugation - Glucose Conjugation 2 [3]
Liquiritin metabolite M4 DM005512
568989
Multi-steps Reaction - Hydrogenation; deoxygenation 2 [2]
Liquiritin metabolite M5 DM005511
13058505
Conjugation - Methylationn 2 [2]
Liquiritin metabolite M6 DM005513
5271544
Conjugation - Methylationn 2 [2]
Liquiritin metabolite M8 DM005508
442342
Reduction - Hydrogenation 2 [3]
Liquiritin metabolite M9 DM005503
10394
Other reaction - Ring cleavage reaction 2 [3]
4-Hydroxybenzoic acid DM004023
135
Other reaction - Degradation 3 [3]
p-Coumaric acid DM003945
637542
Oxidation - Dehydrogenation 3 [3]
4-Hydroxyhippuric acid DM003392
151012
Other reaction - Amino acid 4 [3]
Liquiritin metabolite M14 DM005506
60081072
Other reaction - Amino acid 4 [3]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005871 Liquiritin Liquiritin metabolite M7 Multi-steps Reaction - Ring cleavage reaction; hydrolysis Unclear [3]
MR005879 Liquiritin Liquiritin metabolite M3 Oxidation - Deglycosylation Unclear [2], [3]
MR005883 Liquiritin Liquiritin metabolite M2 Conjugation - Acetylation Unclear [2]
MR005880 Liquiritin metabolite M3 Liquiritin metabolite M5 Conjugation - Methylationn Unclear [2]
MR005881 Liquiritin metabolite M3 Liquiritin metabolite M4 Multi-steps Reaction - Hydrogenation; deoxygenation Unclear [2]
MR005882 Liquiritin metabolite M3 Liquiritin metabolite M6 Conjugation - Methylationn Unclear [2]
MR005872 Liquiritin metabolite M7 Liquiritin metabolite M9 Other reaction - Ring cleavage reaction Unclear [3]
MR005877 Liquiritin metabolite M7 Liquiritin metabolite M8 Reduction - Hydrogenation Unclear [3]
MR005878 Liquiritin metabolite M7 Liquiritin metabolite M12 Conjugation - Glucose Conjugation Unclear [3]
MR005873 Liquiritin metabolite M9 Liquiritin metabolite M11 Other reaction - Degradation Unclear [3]
MR005876 Liquiritin metabolite M9 Liquiritin metabolite M10 Oxidation - Dehydrogenation Unclear [3]
MR005874 Liquiritin metabolite M11 Liquiritin metabolite M13 Other reaction - Amino acid Unclear [3]
MR005875 Liquiritin metabolite M11 Liquiritin metabolite M14 Other reaction - Amino acid Unclear [3]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1253 Bacteroides oleiciplenus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1739 Bacillus subtilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1742 Clostridium algifaecis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1743 Veillonella parvula Not Available Not Available [2]
References
1 Liquiritin from Glycyrrhiza uralensis attenuating rheumatoid arthritis via reducing inflammation, suppressing angiogenesis, and inhibiting MAPK signaling pathway. J Agric Food Chem. 2019 Mar 13;67(10):2856-2864.
2 Effect of liquiritin on human intestinal bacteria growth: metabolism and modulation. Biomed Chromatogr. 2014 Sep;28(9):1271-7.
3 A comprehensive profiling and identification of liquiritin metabolites in rats using ultra-high-performance liquid chromatography coupled with linear ion trap-orbitrap mass spectrometer

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