Identification

Name
Emodin
Accession Number
DB07715  (DB12653)
Type
Small Molecule
Groups
Investigational
Description

Emodin has been investigated for the treatment of Polycystic Kidney.

Structure
Thumb
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
Categories
UNII
KA46RNI6HN
CAS number
518-82-1
Weight
Average: 270.2369
Monoisotopic: 270.05282343
Chemical Formula
C15H10O5
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCasein kinase II subunit alphaNot AvailableHuman
UPutative ketoacyl reductaseNot AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
U3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZNot AvailableHelicobacter pylori
UAryl hydrocarbon receptor
agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Emodin.
AclidiniumThe therapeutic efficacy of Emodin can be decreased when used in combination with Aclidinium.
AgmatineThe therapeutic efficacy of Emodin can be decreased when used in combination with Agmatine.
AlcuroniumThe therapeutic efficacy of Emodin can be decreased when used in combination with Alcuronium.
AlfentanilThe therapeutic efficacy of Emodin can be decreased when used in combination with Alfentanil.
AlphacetylmethadolThe therapeutic efficacy of Emodin can be decreased when used in combination with Alphacetylmethadol.
AlphaprodineThe therapeutic efficacy of Emodin can be decreased when used in combination with Alphaprodine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Emodin.
AmiodaroneThe therapeutic efficacy of Emodin can be decreased when used in combination with Amiodarone.
AmitriptylineThe therapeutic efficacy of Emodin can be decreased when used in combination with Amitriptyline.
Food Interactions
Not Available

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
HET
EMO
Wikipedia
Emodin
PDB Entries
1f0q / 2rh4 / 2rhc / 2rhr / 3bqc / 3c13 / 3csd / 3ed0 / 3pzh / 3q9w
show 2 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableTerminatedTreatmentKidney, Polycystic1

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
PropertyValueSource
Water Solubility0.222 mg/mLALOGPS
logP2.66ALOGPS
logP3.82ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.29ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.13 m3·mol-1ChemAxon
Polarizability26.58 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9878
Blood Brain Barrier+0.5663
Caco-2 permeable+0.7801
P-glycoprotein substrateSubstrate0.5422
P-glycoprotein inhibitor INon-inhibitor0.9619
P-glycoprotein inhibitor IINon-inhibitor0.9432
Renal organic cation transporterNon-inhibitor0.9058
CYP450 2C9 substrateNon-substrate0.7113
CYP450 2D6 substrateNon-substrate0.8963
CYP450 3A4 substrateNon-substrate0.66
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8825
CYP450 2D6 inhibitorNon-inhibitor0.6118
CYP450 2C19 inhibitorNon-inhibitor0.5367
CYP450 3A4 inhibitorNon-inhibitor0.5424
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6156
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.8902
BiodegradationNot ready biodegradable0.7857
Rat acute toxicity2.5826 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9449
hERG inhibition (predictor II)Non-inhibitor0.8974
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-cd1368af6fd71ad45899
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-2f7fb214594d9dd58ff6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-106r-2090000000-9b129a417bc060d33cc1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-48e785e66af8396f4347
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-2524a49c780104535532
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gdi-2090000000-eb5ce4ed15fb44771926
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-7b75ac0aede192dc2ee6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-4df9d81040eb8a48e65c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-7b8f9b479ca718fde6ee
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-0290000000-88fa3da245399884b6bc
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-009e-0960000000-93c437b387d3e1aa7d90
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0090000000-79e91c5055c98d8e3db0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0090000000-bdb88728428b2b7baa22
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0090000000-9da9425656e26f3ca941
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-8c9267f9d7e631944de2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-c886ca3730f953370e44
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0190000000-41f1d89cf454e5ae7574
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-002b-0940000000-780c17885ad8db4f5a18
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-2e61cf51b55f218dea78
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ufr-0190000000-6c97fd1b1144abdb9fed
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0umi-0190000000-fc4d25dd0d6b00a0dbc0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05fr-1490000000-7d7df50c05fdc5d6767a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05fr-1490000000-6dbcbd8581ffa5701094
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0101-2940000000-4b0a267fa20f8d45f167
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0590000000-c5a80156c2fb19e92afe

Taxonomy

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
Hydroxyanthraquinone / Aryl ketone / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Vinylogous acid / Ketone / Polyol / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
hydroxyanthraquinones (CHEBI:42223) / Anthracenes and phenanthrenes, Anthraquinone type (C10343) / Anthracenes and phenanthrenes (LMPK13040008)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific 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 ser...
Gene Name
CSNK2A1
Uniprot ID
P68400
Uniprot Name
Casein kinase II subunit alpha
Molecular Weight
45143.25 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Not Available
Gene Name
actIII
Uniprot ID
P16544
Uniprot Name
Putative ketoacyl reductase
Molecular Weight
27264.88 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activity
Specific 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.Involved in unsaturat...
Gene Name
fabZ
Uniprot ID
Q5G940
Uniprot Name
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ
Molecular Weight
18184.08 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. 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. [PubMed:14644660]

Drug created on September 15, 2010 15:25 / Updated on November 02, 2018 06:37