Emodin
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Identification
- Generic Name
- Emodin
- DrugBank Accession Number
- DB07715
- Background
Emodin has been investigated for the treatment of Polycystic Kidney.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 270.2369
Monoisotopic: 270.05282343 - Chemical Formula
- C15H10O5
- Synonyms
- 1,3,8-trihydroxy-6-methyl-9,10-anthracenedione
- 1,3,8-trihydroxy-6-methyl-9,10-anthraquinone
- Schuttgelb
- External IDs
- NSC-408120
- NSC-622947
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ACasein kinase II subunit alpha inhibitorHumans UPutative ketoacyl reductase Not Available Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) U3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ Not Available Helicobacter pylori UAryl hydrocarbon receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The risk or severity of dehydration can be increased when Acetazolamide is combined with Emodin. Aclidinium The therapeutic efficacy of Emodin can be decreased when used in combination with Aclidinium. Alfentanil The therapeutic efficacy of Emodin can be decreased when used in combination with Alfentanil. Alloin The risk or severity of adverse effects can be increased when Emodin is combined with Alloin. Amantadine The therapeutic efficacy of Emodin can be decreased when used in combination with Amantadine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as hydroxyanthraquinones. These are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Anthracenes
- Sub Class
- Anthraquinones
- Direct Parent
- Hydroxyanthraquinones
- Alternative Parents
- Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Polyols / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homopolycyclic compound / Aryl ketone / Hydrocarbon derivative / Hydroxyanthraquinone / Ketone / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- hydroxyanthraquinones (CHEBI:42223) / Anthracenes and phenanthrenes, Anthraquinone type (C10343) / Anthracenes and phenanthrenes (LMPK13040008)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- KA46RNI6HN
- CAS number
- 518-82-1
- InChI Key
- RHMXXJGYXNZAPX-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
- IUPAC Name
- 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione
- SMILES
- CC1=CC(O)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0035214
- KEGG Compound
- C10343
- PubChem Compound
- 3220
- PubChem Substance
- 99444186
- ChemSpider
- 3107
- BindingDB
- 11318
- ChEBI
- 42223
- ChEMBL
- CHEMBL289277
- ZINC
- ZINC000003824868
- PDBe Ligand
- EMO
- Wikipedia
- Emodin
- PDB Entries
- 1f0q / 2rh4 / 2rhc / 2rhr / 3bqc / 3c13 / 3csd / 3ed0 / 3pzh / 3q9w … show 4 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Terminated Treatment Kidney, Polycystic 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.222 mg/mL ALOGPS logP 2.66 ALOGPS logP 3.82 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 7.29 Chemaxon pKa (Strongest Basic) -5.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 72.13 m3·mol-1 Chemaxon Polarizability 26.58 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9878 Blood Brain Barrier + 0.5663 Caco-2 permeable + 0.7801 P-glycoprotein substrate Substrate 0.5422 P-glycoprotein inhibitor I Non-inhibitor 0.9619 P-glycoprotein inhibitor II Non-inhibitor 0.9432 Renal organic cation transporter Non-inhibitor 0.9058 CYP450 2C9 substrate Non-substrate 0.7113 CYP450 2D6 substrate Non-substrate 0.8963 CYP450 3A4 substrate Non-substrate 0.66 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8825 CYP450 2D6 inhibitor Non-inhibitor 0.6118 CYP450 2C19 inhibitor Non-inhibitor 0.5367 CYP450 3A4 inhibitor Non-inhibitor 0.5424 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6156 Ames test AMES toxic 0.9108 Carcinogenicity Non-carcinogens 0.8902 Biodegradation Not ready biodegradable 0.7857 Rat acute toxicity 2.5826 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9449 hERG inhibition (predictor II) Non-inhibitor 0.8974
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.8447907 predictedDarkChem Lite v0.1.0 [M-H]- 152.6837559 predictedDarkChem Standard v0.1.0 [M-H]- 151.8855316 predictedDarkChem Lite v0.1.0 [M-H]- 170.8421907 predictedDarkChem Lite v0.1.0 [M-H]- 170.9289907 predictedDarkChem Lite v0.1.0 [M-H]- 160.14413 predictedDeepCCS 1.0 (2019) [M+H]+ 172.1407907 predictedDarkChem Lite v0.1.0 [M+H]+ 156.8332436 predictedDarkChem Standard v0.1.0 [M+H]+ 158.9147546 predictedDarkChem Lite v0.1.0 [M+H]+ 173.8561907 predictedDarkChem Lite v0.1.0 [M+H]+ 173.4214907 predictedDarkChem Lite v0.1.0 [M+H]+ 162.50214 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.5860907 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.6381907 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.3041535 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.6611907 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.5845907 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.82515 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsCasein kinase II subunit alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalytic subunit of a constitutively active serine/threonine-protein kinase complex that phosphorylates a large number of substrates containing acidic residues C-terminal to the phosphorylated serine or threonine (PubMed:11239457, PubMed:11704824, PubMed:16193064, PubMed:18411307, PubMed:18583988, PubMed:18678890, PubMed:19188443, PubMed:20545769, PubMed:20625391, PubMed:22017874, PubMed:22406621, PubMed:24962073, PubMed:30898438, PubMed:31439799). Regulates numerous cellular processes, such as cell cycle progression, apoptosis and transcription, as well as viral infection (PubMed:12631575, PubMed:19387551, PubMed:19387552). May act as a regulatory node which integrates and coordinates numerous signals leading to an appropriate cellular response (PubMed:12631575, PubMed:19387551, PubMed:19387552). During mitosis, functions as a component of the p53/TP53-dependent spindle assembly checkpoint (SAC) that maintains cyclin-B-CDK1 activity and G2 arrest in response to spindle damage (PubMed:11704824, PubMed:19188443). Also required for p53/TP53-mediated apoptosis, phosphorylating 'Ser-392' of p53/TP53 following UV irradiation (PubMed:11239457). Phosphorylates a number of DNA repair proteins in response to DNA damage, such as MDC1, MRE11, RAD9A, RAD51 and HTATSF1, promoting their recruitment to DNA damage sites (PubMed:18411307, PubMed:18583988, PubMed:18678890, PubMed:20545769, PubMed:21482717, PubMed:22325354, PubMed:26811421, PubMed:28512243, PubMed:30898438, PubMed:35597237). Can also negatively regulate apoptosis (PubMed:16193064, PubMed:22184066). Phosphorylates the caspases CASP9 and CASP2 and the apoptotic regulator NOL3 (PubMed:16193064). Phosphorylation protects CASP9 from cleavage and activation by CASP8, and inhibits the dimerization of CASP2 and activation of CASP8 (PubMed:16193064). Phosphorylates YY1, protecting YY1 from cleavage by CASP7 during apoptosis (PubMed:22184066). Regulates transcription by direct phosphorylation of RNA polymerases I, II, III and IV (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552, PubMed:23123191). Also phosphorylates and regulates numerous transcription factors including NF-kappa-B, STAT1, CREB1, IRF1, IRF2, ATF1, ATF4, SRF, MAX, JUN, FOS, MYC and MYB (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552, PubMed:23123191). Phosphorylates Hsp90 and its co-chaperones FKBP4 and CDC37, which is essential for chaperone function (PubMed:19387550). Mediates sequential phosphorylation of FNIP1, promoting its gradual interaction with Hsp90, leading to activate both kinase and non-kinase client proteins of Hsp90 (PubMed:30699359). Regulates Wnt signaling by phosphorylating CTNNB1 and the transcription factor LEF1 (PubMed:19387549). Acts as an ectokinase that phosphorylates several extracellular proteins (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552). During viral infection, phosphorylates various proteins involved in the viral life cycles of EBV, HSV, HBV, HCV, HIV, CMV and HPV (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552). Phosphorylates PML at 'Ser-565' and primes it for ubiquitin-mediated degradation (PubMed:20625391, PubMed:22406621). Plays an important role in the circadian clock function by phosphorylating BMAL1 at 'Ser-90' which is pivotal for its interaction with CLOCK and which controls CLOCK nuclear entry (By similarity). Phosphorylates CCAR2 at 'Thr-454' in gastric carcinoma tissue (PubMed:24962073). Phosphorylates FMR1, promoting FMR1-dependent formation of a membraneless compartment (PubMed:30765518, PubMed:31439799). May phosphorylate histone H2A on 'Ser-1' (PubMed:38334665)
- Specific Function
- ATP binding
- Gene Name
- CSNK2A1
- Uniprot ID
- P68400
- Uniprot Name
- Casein kinase II subunit alpha
- Molecular Weight
- 45143.25 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsPutative ketoacyl reductase
- Kind
- Protein
- Organism
- Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- oxidoreductase activity
- Gene Name
- actIII
- Uniprot ID
- P16544
- Uniprot Name
- Putative ketoacyl reductase
- Molecular Weight
- 27264.88 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Helicobacter pylori
- Pharmacological action
- Unknown
- General Function
- Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs.
- Specific Function
- (3R)-hydroxyacyl-[acyl-carrier-protein] dehydratase activity
- Gene Name
- fabZ
- Uniprot ID
- Q5G940
- Uniprot Name
- 3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ
- Molecular Weight
- 18184.08 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
4. DetailsAryl hydrocarbon receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Ligand-activated transcription factor that enables cells to adapt to changing conditions by sensing compounds from the environment, diet, microbiome and cellular metabolism, and which plays important roles in development, immunity and cancer (PubMed:23275542, PubMed:30373764, PubMed:32818467, PubMed:7961644). Upon ligand binding, translocates into the nucleus, where it heterodimerizes with ARNT and induces transcription by binding to xenobiotic response elements (XRE) (PubMed:23275542, PubMed:30373764, PubMed:7961644). Regulates a variety of biological processes, including angiogenesis, hematopoiesis, drug and lipid metabolism, cell motility and immune modulation (PubMed:12213388). Xenobiotics can act as ligands: upon xenobiotic-binding, activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene) (PubMed:7961644). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons (PubMed:34521881, PubMed:7961644). Next to xenobiotics, natural ligands derived from plants, microbiota, and endogenous metabolism are potent AHR agonists (PubMed:18076143). Tryptophan (Trp) derivatives constitute an important class of endogenous AHR ligands (PubMed:32818467, PubMed:32866000). Acts as a negative regulator of anti-tumor immunity: indoles and kynurenic acid generated by Trp catabolism act as ligand and activate AHR, thereby promoting AHR-driven cancer cell motility and suppressing adaptive immunity (PubMed:32818467). Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1 (PubMed:28602820). Inhibits PER1 by repressing the CLOCK-BMAL1 heterodimer mediated transcriptional activation of PER1 (PubMed:28602820). The heterodimer ARNT:AHR binds to core DNA sequence 5'-TGCGTG-3' within the dioxin response element (DRE) of target gene promoters and activates their transcription (PubMed:28602820)
- Specific Function
- cis-regulatory region sequence-specific DNA binding
- Gene Name
- AHR
- Uniprot ID
- P35869
- Uniprot Name
- Aryl hydrocarbon receptor
- Molecular Weight
- 96146.705 Da
References
- Zhang S, Qin C, Safe SH: Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. Environ Health Perspect. 2003 Dec;111(16):1877-82. [Article]
Drug created at September 15, 2010 21:25 / Updated at August 26, 2024 19:24