Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D0L4FS
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| Former ID |
DCL000330
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| Drug Name |
Genistein
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| Synonyms |
Bonistein; GEN; Genestein; Genisteol; Genisterin; Prunetol; Sophoricol; Differenol A; G 6649; G10000; IN1327; NPI 031L; STO514; TNP00151; GENISTEIN (ENDOCRINE DISRUPTER); Lactoferrin-genistein; PTI G4660 (Genistein); PTI-G4660; SIPI 807-1; C.I. 75610; SIPI-9764-I; ENDOCRINE DISRUPTOR (GENISTEIN) (SEE ALSO GENISTEIN (446-72-0)); 4 inverted exclamation marka,5,7-Trihydroxyisoflavone; ,5,7-Trihydroxyisoflavone; 4',5, 7-Trihydroxyisoflavone; 4',5,7-Trihydroxy isoflavone; 4',5,7-Trihydroxyisoflavone; 4,5,7-Trihydroxyiso-flavone; 4,6,7-Trihydroxyisoflavone; 5,7,4'-Trihydroxyisoflavone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
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| Drug Type |
Small molecular drug
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| Indication | Menopause symptom [ICD-11: GA30.0] | Phase 2/3 | [1] | |
| Prostate cancer [ICD-11: 2C82.0; ICD-10: C61; ICD-9: 185] | Phase 2 | [2], [3] | ||
| Company |
DSM Nutritional Products
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| Structure |
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Download2D MOL |
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| Formula |
C15H10O5
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| Canonical SMILES |
C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
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| InChI |
1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
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| InChIKey |
TZBJGXHYKVUXJN-UHFFFAOYSA-N
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| CAS Number |
CAS 446-72-0
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| PubChem Compound ID | ||||
| PubChem Substance ID |
8792, 93197, 606653, 640215, 854585, 854586, 3153130, 4652582, 7887819, 8138208, 8144401, 8616462, 10318994, 11111233, 11111234, 11113921, 11114608, 11120325, 11120813, 11121301, 11341576, 11361759, 11363214, 11364972, 11365776, 11367534, 11368338, 11370096, 11371695, 11373135, 11375144, 11375696, 11376500, 11378267, 11404364, 11407761, 11484372, 11487161, 11488454, 11490494, 11493357, 11494134, 15197341, 17389520, 17405083, 22391506, 24278036, 24895273, 25622056, 26527427
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| ChEBI ID |
CHEBI:28088
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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): Bacteroidales | ||||
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Studied Microbe: Bacteroides uniformis
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[4] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrogenation | |||
| Resulting Metabolite | 5-hydroxy-equol | |||
| Description | Genistein can be metabolized to 5-hydroxy-equol by Bacteroides uniformis through hydrogenation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Adlercreutzia equolifaciens
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[5] | |||
| Hierarchy | ||||
| Resulting Metabolite | 5-hydroxy-equol | |||
| Description | Genistein can be metabolized to 5-hydroxy-equol by Adlercreutzia equolifaciens. | |||
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Studied Microbe: Slackia equolifaciens
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[5] | |||
| Hierarchy | ||||
| Resulting Metabolite | 5-hydroxy-equol | |||
| Description | Genistein can be metabolized to 5-hydroxy-equol by Slackia equolifaciens. | |||
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Studied Microbe: Slackia isoflavoniconvertens
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[5] | |||
| Hierarchy | ||||
| Resulting Metabolite | 5-hydroxy-equol | |||
| Description | Genistein can be metabolized to 5-hydroxy-equol by Slackia isoflavoniconvertens. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Eubacterium ramulus
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[6] | |||
| Hierarchy | ||||
| Resulting Metabolite | 2--(4-hydroxyphenyl)-propionic-acid | |||
| Metabolic Effect | Decrease activity | |||
| Description | Genistein can be metabolized to 2--(4-hydroxyphenyl)-propionic-acid by Eubacterium ramulus, which results in the decrease of the drug's activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactococcus garvieae
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|
[5] | |||
| Hierarchy | ||||
| Resulting Metabolite | 5-hydroxy-equol | |||
| Description | Genistein can be metabolized to 5-hydroxy-equol by Lactococcus garvieae. | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides acidifaciens
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Bacteroides acidifaciens was increased by Genistein (p < 0.0001). | |||
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Studied Microbe: Bacteroides uniformis
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Bacteroides uniformis was increased by Genistein (p < 0.0001). | |||
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Studied Microbe: Parabacteroides distasonis
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Parabacteroides distasonis was increased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium longum
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Bifidobacterium longum was decreased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Campylobacterales | ||||
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Studied Microbe: Helicobacter apodemus
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Helicobacter apodemus was increased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Collinsella aerofaciens
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Deferribacterales | ||||
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Studied Microbe: Mucispirillum schaedleri
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Mucispirillum schaedleri was increased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Blautia obeum was decreased by Genistein (p < 0.0001). | |||
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Studied Microbe: Butyricicoccus pullicaecorum
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Butyricicoccus pullicaecorum was increased by Genistein (p < 0.0001). | |||
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Studied Microbe: Enterocloster citroniae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Enterocloster citroniae was decreased by Genistein (p < 0.0001). | |||
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Studied Microbe: Roseburia faecis
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Roseburia faecis was decreased by Genistein (p < 0.0001). | |||
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Studied Microbe: Ruminococcus bromii
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Ruminococcus bromii was increased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Limosilactobacillus reuteri
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Limosilactobacillus reuteri was increased by Genistein (p < 0.0001). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Verrucomicrobiales | ||||
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Studied Microbe: Akkermansia muciniphila
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Obesity | |||
| Description | The abundance of Akkermansia muciniphila was increased by Genistein (p < 0.0001). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Estrogen receptor beta (ESR2) | Target Info | Modulator | [8] |
| KEGG Pathway | Estrogen signaling pathway | |||
| Prolactin signaling pathway | ||||
| Pathway Interaction Database | Plasma membrane estrogen receptor signaling | |||
| Validated nuclear estrogen receptor beta network | ||||
| Validated nuclear estrogen receptor alpha network | ||||
| Reactome | Nuclear Receptor transcription pathway | |||
| WikiPathways | SIDS Susceptibility Pathways | |||
| Ovarian Infertility Genes | ||||
| Integrated Pancreatic Cancer Pathway | ||||
| Nuclear Receptors | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | ClinicalTrials.gov (NCT00355953) Vascular and Skeletal Protective Effects of Genistein in Postmenopausal Women. U.S. National Institutes of Health. | |||
| REF 2 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2826). | |||
| REF 3 | New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202. | |||
| REF 4 | The influence of gut microbiota on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol. 2016;12(1):31-40. | |||
| REF 5 | Gut Microbiota-Mediated Drug-Antibiotic Interactions. Drug Metab Dispos. 2015 Oct;43(10):1581-9. | |||
| REF 6 | Pharmacomicrobiomics: The Holy Grail to Variability in Drug Response?. Clin Pharmacol Ther. 2019 Aug;106(2):317-328. | |||
| REF 7 | Genistein stimulates insulin sensitivity through gut microbiota reshaping and skeletal muscle AMPK activation in obese subjects. BMJ Open Diabetes Res Care. 2020 Mar;8(1):e000948. | |||
| REF 8 | Company report (Axcentua) | |||
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