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

General Information of Drug (ID: DR2206)
Drug Name
DB-041901
Synonyms
Pursennid; Senekot; Senna-lax; Sennaglucosides; Sennosides; Sennoside A&B; Sennoside [JAN]; Sennosides A and B; sennoside; (9,9'-Bianthracene)-2,2'-dicarboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-; 5,5'-Bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy(9,9'-bianthrachinon)-2,2'-dicarbonsaeure; 5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo(9,9'-bianthracene)-2,2'-dicarboxylic acid; 517-43-1; C42H38O20; EINECS 208-238-9; SENNA
Indication Opioid-induced constipation [ICD11: DB32] Phase 2 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 862.7 Topological Polar Surface Area 348
Heavy Atom Count 62 Rotatable Bond Count 9
Hydrogen Bond Donor Count 12 Hydrogen Bond Acceptor Count 20
Cross-matching ID
PubChem CID
5199
CAS Number
517-43-1
Formula
C42H38O20
Canonical SMILES
C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O
InChI
1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)
InChIKey
IPQVTOJGNYVQEO-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
8-glucosyl-rheinanthrone DM006856 N. A. Unclear 1 [3]
Sennidin-8-monoglucoside DM006852 N. A. Hydrolysis - Hydrolysis 1 [4]
Rhein DM006855
10168
Unclear 2 [3]
Sennidins DM006853 N. A. Unclear 2 [3]
Rheinanthrone DM006854
119396
Unclear 3 [5]
Rhein DM006855
10168
Oxidation - Oxidationn 4 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007439 DB-041901 Sennidin-8-monoglucoside Hydrolysis - Hydrolysis bglA [4]
MR007443 DB-041901 8-glucosyl-rheinanthrone Unclear Unclear [3]
MR007444 8-glucosyl-rheinanthrone Rhein Unclear Unclear [3]
MR007440 Sennidin-8-monoglucoside Sennidins Unclear Unclear [3]
MR007441 Sennidins Rheinanthrone Unclear bglA [5]
MR007442 Rheinanthrone Rhein Oxidation - Oxidationn Unclear [5]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-glucosidase (bglA) DME1842 Bacteroides thetaiotaomicron
A0A0P0FEZ9_BACT4
3.2.1.21
[2]
References
1 ClinicalTrials.gov (NCT02239510) Efficacy of Linaclotide to Senna for CIC
2 Gut microbiota-mediated drug-antibiotic interactions. Drug Metab Dispos. 2015 Oct;43(10):1581-9.
3 Metabolism of sennosides by human intestinal bacteria
4 The action of sennosides and related compounds on human colon and rectum
5 Rheinanthrone, a metabolite of sennoside A, triggers macrophage activation to decrease aquaporin-3 expression in the colon, causing the laxative effect of rhubarb extract

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