Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D09ALJ
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| Former ID |
DNC002677
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| Drug Name |
Rutin
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| Synonyms |
RUTIN; 153-18-4; rutoside; Phytomelin; Quercetin 3-rutinoside; Birutan; Eldrin; Rutin trihydrate; Myrticolorin; Venoruton; Bioflavonoid; Paliuroside; Tanrutin; Osyritrin; Rutine; Rutozyd; 3-Rutinosyl quercetin; 3-Rhamnoglucosylquercetin; Quercetin 3-O-rutinoside; Rutosido; Rutosidum; Rutinum; Globularicitrin; Quercetin-3-rutinoside; Rutabion; Violaquercitrin; Globulariacitrin; Melin; Rutinic acid; Birutan Forte; Birutin; Quercetin rhamnoglucosine; Quercetin-3beta-rutinoside; UNII-5G06TVY3R7; Oxyritin; Rutosid; Ilixanthin; Rutinion acid
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| Drug Type |
Small molecular drug
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| Indication | Discovery agent [ICD-11: N.A.] | Investigative | [1] | |
| Structure |
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Download2D MOL |
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| Formula |
C27H30O16
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| Canonical SMILES |
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
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| InChI |
1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
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| InChIKey |
IKGXIBQEEMLURG-NVPNHPEKSA-N
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| CAS Number |
CAS 153-18-4
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| PubChem Compound ID | ||||
| PubChem Substance ID |
7941, 583769, 597190, 7890342, 8149167, 8616403, 11335819, 11361058, 11462030, 12015663, 14789521, 14936333, 24775672, 26719694, 29204545, 29216321, 39289828, 46386546, 47365182, 47588990, 47885411, 48414436, 48421832, 49681540, 50077472, 50077674, 50696375, 53789070, 57357881, 57394649, 85842433, 87575608, 88783231, 92297747, 92308256, 93165829, 93167038, 95154018, 96025184, 99301732, 103516775, 104091802, 104253605, 113854033, 124658987, 124757744, 124892311, 125164548, 126524764, 126688137
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| ChEBI ID |
CHEBI:28527
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacillales | ||||
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Studied Microbe: Bacillus sp. 52
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[2] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucosidase and alpha-L-rhamnosidase | |||
| Metabolic Reaction | Deglycosylation | |||
| Resulting Metabolite | Quercetin 3-O-glucoside; leucocyanidin | |||
| Description | Rutin can be metabolized to Quercetin 3-O-glucoside and leucocyanidin by the beta glucosidase and alpha-L-rhamnosidase of Bacillus sp. 52 through deglycosylation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides
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[3] | |||
| Hierarchy | ||||
| Metabolic Reaction | Glycosidic bond generation | |||
| Resulting Metabolite | Quercetin | |||
| Description | Rutin can be metabolized to Quercetin by Bacteroides through glycosidic bond generation. | |||
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Studied Microbe: Bacteroides JY-6
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Description | Rutin can be metabolized to Quercetin, 4-hydroxybenzoic acid, 3,4-dDihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Bacteroides JY-6. | |||
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Studied Microbe: Bacteroides ovatus
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[5] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | Quercetin-aglycone; polyphenols | |||
| Metabolic Effect | Induce mutagenicity | |||
| Description | Rutin can be metabolized to Quercetin-aglycone and polyphenols by Bacteroides ovatus through hydrolysis, which results in the induction of the drug's mutagenicity. | |||
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Studied Microbe: Bacteroides sp
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[2] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucosidase and alpha-L-rhamnosidase | |||
| Metabolic Reaction | Deglycosylation | |||
| Resulting Metabolite | Quercetin 3-O-glucoside; leucocyanidin | |||
| Description | Rutin can be metabolized to Quercetin 3-O-glucoside and leucocyanidin by the beta glucosidase and alpha-L-rhamnosidase of Bacteroides sp through deglycosylation. | |||
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Studied Microbe: Bacteroides sp. 22
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[2] | |||
| Hierarchy | ||||
| Microbial Enzyme | Alpha-L-rhamnosidase | |||
| Metabolic Reaction | Deglycosylation | |||
| Resulting Metabolite | Quercetin-3-O-glucoside | |||
| Description | Rutin can be metabolized to Quercetin-3-O-glucoside by the alpha-L-rhamnosidase of Bacteroides sp. 22 through deglycosylation. | |||
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Studied Microbe: Bacteroides sp. 45
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[2] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucosidase and alpha-L-rhamnosidase | |||
| Metabolic Reaction | Deglycosylation | |||
| Resulting Metabolite | Quercetin 3-O-glucoside; leucocyanidin | |||
| Description | Rutin can be metabolized to Quercetin 3-O-glucoside and leucocyanidin by the beta glucosidase and alpha-L-rhamnosidase of Bacteroides sp. 45 through deglycosylation. | |||
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Studied Microbe: Bacteroides uniformis
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[5] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | Quercetin-aglycone; polyphenols | |||
| Metabolic Effect | Induce mutagenicity | |||
| Description | Rutin can be metabolized to Quercetin-aglycone and polyphenols by Bacteroides uniformis through hydrolysis, which results in the induction of the drug's mutagenicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium B-9
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Description | Rutin can be metabolized to Quercetin, 4-hydroxybenzoic acid, 3,4-dDihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Bifidobacterium B-9. | |||
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Studied Microbe: Bifidobacterium dentium
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[6], [7] | |||
| Hierarchy | ||||
| Microbial Enzyme | Alpha-L-rhamnosidase | |||
| Metabolic Effect | Decrease activity | |||
| Description | Rutin can be metabolized by the alpha-L-rhamnosidase of Bifidobacterium dentium, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Bifidobacterium sp.
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[3] | |||
| Hierarchy | ||||
| Metabolic Reaction | Glycosidic bond generation | |||
| Resulting Metabolite | Quercetin | |||
| Description | Rutin can be metabolized to Quercetin by Bifidobacterium sp. through glycosidic bond generation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Butyrivibrio sp.
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[5] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | Quercetin-aglycone; polyphenols | |||
| Metabolic Effect | Induce mutagenicity | |||
| Description | Rutin can be metabolized to Quercetin-aglycone and polyphenols by Butyrivibrio sp. through hydrolysis, which results in the induction of the drug's mutagenicity. | |||
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Studied Microbe: Clostridium
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[3] | |||
| Hierarchy | ||||
| Metabolic Reaction | Glycosidic bond generation | |||
| Resulting Metabolite | Quercetin | |||
| Description | Rutin can be metabolized to Quercetin by Clostridium through glycosidic bond generation. | |||
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Studied Microbe: Eubacterium
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[3] | |||
| Hierarchy | ||||
| Metabolic Reaction | Glycosidic bond generation | |||
| Resulting Metabolite | Quercetin | |||
| Description | Rutin can be metabolized to Quercetin by Eubacterium through glycosidic bond generation. | |||
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Studied Microbe: Eubacterium YK-4
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Description | Rutin can be metabolized to Quercetin, 4-hydroxybenzoic acid, 3,4-dDihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Eubacterium YK-4. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Fusobacteriales | ||||
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Studied Microbe: Fusobacterium K-60
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Description | Rutin can be metabolized to Quercetin, 4-hydroxybenzoic acid, 3,4-dDihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Fusobacterium K-60. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus
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[3] | |||
| Hierarchy | ||||
| Metabolic Reaction | Glycosidic bond generation | |||
| Resulting Metabolite | Quercetin | |||
| Description | Rutin can be metabolized to Quercetin by Lactobacillus through glycosidic bond generation. | |||
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Studied Microbe: Lactobacillus sp. L2
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Description | Rutin can be metabolized to Quercetin, 4-hydroxybenzoic acid, 3,4-dDihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Lactobacillus sp. L2. | |||
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Studied Microbe: Streptococcus sp. S2
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[4] | |||
| Hierarchy | ||||
| Resulting Metabolite | Quercetin; 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid; 3,4-dihydroxyphenylacetic acid | |||
| Metabolic Effect | Increase activity | |||
| Description | Rutin can be metabolized to Quercetin and 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid and 3,4-dihydroxyphenylacetic acid by Streptococcus sp. S2, which results in the increase of the drug's activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Veillonella sp. R-32
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[2] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucosidase and alpha-L-rhamnosidase | |||
| Metabolic Reaction | Deglycosylation | |||
| Resulting Metabolite | Quercetin 3-O-glucoside; leucocyanidin | |||
| Description | Rutin can be metabolized to Quercetin 3-O-glucoside and leucocyanidin by the beta glucosidase and alpha-L-rhamnosidase of Veillonella sp. R-32 through deglycosylation. | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Dihydrodiol dehydrogenase type I (AKR1C3) | Target Info | Inhibitor | [1] |
| BioCyc | Superpathway of steroid hormone biosynthesis | |||
| Allopregnanolone biosynthesis | ||||
| Androgen biosynthesis | ||||
| KEGG Pathway | Steroid hormone biosynthesis | |||
| Arachidonic acid metabolism | ||||
| Metabolic pathways | ||||
| Ovarian steroidogenesis | ||||
| NetPath Pathway | TGF_beta_Receptor Signaling Pathway | |||
| Pathwhiz Pathway | Arachidonic Acid Metabolism | |||
| Reactome | Retinoid metabolism and transport | |||
| WikiPathways | Metapathway biotransformation | |||
| Benzo(a)pyrene metabolism | ||||
| Arachidonic acid metabolism | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6. | |||
| REF 2 | Identification of rutin deglycosylated metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 1;898:95-100. | |||
| REF 3 | Effects of Gut Microbiota on Drug Metabolism and Guidance for Rational Drug Use Under Hypoxic Conditions at High Altitudes. Curr Drug Metab. 2019;20(2):155-165. | |||
| REF 4 | Gut microbiota, a new frontier to understand traditional Chinese medicines. Pharmacol Res. 2019 Apr;142:176-191. | |||
| REF 5 | Gut Pharmacomicrobiomics: the tip of an iceberg of complex interactions between drugs and gut-associated microbes. Gut Pathog. 2012 Nov 30;4(1):16. | |||
| REF 6 | Drug pharmacomicrobiomics and toxicomicrobiomics: from scattered reports to systematic studies of drug-microbiome interactions. Expert Opin Drug Metab Toxicol. 2018 Oct;14(10):1043-1055. | |||
| REF 7 | Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing Alpha-L-rhamnosidase from Bifidobacterium dentium. J Microbiol Biotechnol. 2015 Jan;25(1):18-25. | |||
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