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

General Information of Drug (ID: DR3547)
Drug Name
Berberine
Synonyms
berberine; 2086-83-1; Berberin; Umbellatine; UNII-0I8Y3P32UF; 0I8Y3P32UF; CHEBI:16118; EINECS 218-229-1; Berberal; BRN 3570374; ST055798; 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium; Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-; 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium; Berbamine sulphate acid; CHEMBL12089; 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium; BERBINIUM, 7,8,13,13a-TETRAHYDRO-9,10-DIMETHOXY-2,3-(METHYLE
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 336.4 Topological Polar Surface Area 40.8
Heavy Atom Count 25 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2353
ChEBI ID
CHEBI:16118
CAS Number
2086-83-1
TTD Drug ID
D0W8WB
Formula
C20H18NO4+
Canonical SMILES
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
InChI
InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
InChIKey
YBHILYKTIRIUTE-UHFFFAOYSA-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
3,9-demethylpalmatine DM017749 N. A. Unclear - Unclear 1 [2]
Berberrubine DM015065
72704
Oxidation - Demethylation 1 [2] , [1] , [3]
Columbamine DM015061
72310
Reduction - Reduction 1 [2]
Demethyleneberberine DM014854
2353
Oxidation - Demethylenation 1 [2] , [1]
Dihydroberberine DM017750 N. A. Reduction - Reduction 1 [2]
Jatrorrhizine DM017738 N. A. Reduction - Reduction 1 [2]
Thalfendine DM015410
3084288
Oxidation - Demethylation 1 [2] , [1] , [3]
2,3,10-trihydroxyberberine DM016737
147339878
Oxidation - Demethylation 2 [2] , [1]
2,3,9-trihydroxyberberine DM016276
68071758
Unclear - Unclear 2 [2]
3,10-demethylpalmatine DM017739 N. A. Oxidation - Demethylation 2 [2]
Berberrubine-9-O-beta-D-glucuronide DM017746 N. A. Conjugation - Glucuronidation 2 [2]
Columbamin-2-O-beta-D-glucuronide DM017748 N. A. Unclear - Unclear 2 [2]
Demethyleneberberine-2,3-di-O-beta-D-glucuronide DM017743 N. A. Conjugation - Glucuronidation 2 [2]
Demethyleneberberine-2-O-sulfate DM017742 N. A. Conjugation - Sulfation 2 [2]
Jatrorrhizine-3-O-beta-D-glucuronide DM017744 N. A. Conjugation - Glucuronidation 2 [2]
Jatrorrhizine-3-O-sulfate DM017745 N. A. Conjugation - Sulfation 2 [2]
Palmatine DM014981
19009
Oxidation - Methylation 2 [2]
Thalifendine-10-O-beta-D-glucuronide DM017747 N. A. Conjugation - Glucuronidation 2 [2]
Thalifendine-10-O-sulfate DM016497
102128786
Conjugation - Sulfation 2 [2]
2,3,10-trihydroxyberberine DM016737
147339878
Oxidation - Demethylation 3 [2]
2,3,10-trihydroxyberberine-2-O-sulfate DM017740 N. A. Conjugation - Sulfation 3 [2]
3,10-demethylpalmatine-10-O-sulfate DM017741 N. A. Unclear - Unclear 3 [2]
2,3,10-trihydroxyberberine-2-O-sulfate DM017740 N. A. Conjugation - Sulfation 4 [2]
⏷ Show the Full List of 23  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013774 Berberine Jatrorrhizine Reduction - Reduction Unclear [2]
MR013779 Berberine Demethyleneberberine Oxidation - Demethylenation CYP2D6 ... [2], [1]
MR013787 Berberine Berberrubine Oxidation - Demethylation cyp51B1 ... [2], [1], [3]
MR013789 Berberine Thalfendine Oxidation - Demethylation CYP2D6 ... [2], [1], [3]
MR013792 Berberine Columbamine Reduction - Reduction Unclear [2]
MR013795 Berberine 3,9-demethylpalmatine Unclear - Unclear Unclear [2]
MR013796 Berberine Dihydroberberine Reduction - Reduction Unclear [2]
MR013788 Berberrubine Berberrubine-9-O-beta-D-glucuronide Conjugation - Glucuronidation Unclear [2]
MR013793 Columbamine Columbamin-2-O-beta-D-glucuronide Unclear - Unclear Unclear [2]
MR013794 Columbamine Palmatine Oxidation - Methylation Unclear [2]
MR013780 Demethyleneberberine 2,3,10-trihydroxyberberine Oxidation - Demethylation CYP2D6 ... [2], [1]
MR013781 Demethyleneberberine Demethyleneberberine-2-O-sulfate Conjugation - Sulfation Unclear [2]
MR013782 Demethyleneberberine 2,3,9-trihydroxyberberine Unclear - Unclear Unclear [2]
MR013783 Demethyleneberberine Demethyleneberberine-2,3-di-O-beta-D-glucuronide Conjugation - Glucuronidation Unclear [2]
MR013775 Jatrorrhizine 3,10-demethylpalmatine Oxidation - Demethylation Unclear [2]
MR013784 Jatrorrhizine Jatrorrhizine-3-O-beta-D-glucuronide Conjugation - Glucuronidation Unclear [2]
MR013785 Jatrorrhizine Jatrorrhizine-3-O-sulfate Conjugation - Sulfation Unclear [2]
MR013786 Jatrorrhizine Palmatine Oxidation - Methylation Unclear [2]
MR013790 Thalfendine Thalifendine-10-O-sulfate Conjugation - Sulfation Unclear [2]
MR013791 Thalfendine Thalifendine-10-O-beta-D-glucuronide Conjugation - Glucuronidation Unclear [2]
MR013776 3,10-demethylpalmatine 2,3,10-trihydroxyberberine Oxidation - Demethylation Unclear [2]
MR013778 3,10-demethylpalmatine 3,10-demethylpalmatine-10-O-sulfate Unclear - Unclear Unclear [2]
MR013777 2,3,10-trihydroxyberberine 2,3,10-trihydroxyberberine-2-O-sulfate Conjugation - Sulfation Unclear [2]
⏷ Show the Full List of 23 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[1]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[1]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[1]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[1]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[1]
References
1 CYP2D plays a major role in berberine metabolism in liver of mice and humans
2 The metabolism of berberine and its contribution to the pharmacological effects
3 Transformation of berberine to its demethylated metabolites by the CYP51 enzyme in the gut microbiota

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