Identification
NameEmodin
Accession NumberDB07715  (DB12653)
TypeSmall Molecule
GroupsInvestigational
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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIIKA46RNI6HN
CAS number518-82-1
WeightAverage: 270.2369
Monoisotopic: 270.05282343
Chemical FormulaC15H10O5
InChI KeyRHMXXJGYXNZAPX-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Casein kinase II subunit alphaProteinunknownNot AvailableHumanP68400 details
Putative ketoacyl reductaseProteinunknownNot AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)P16544 details
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZProteinunknownNot AvailableHelicobacter pyloriQ5G940 details
Aryl hydrocarbon receptorProteinunknown
agonist
HumanP35869 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableTerminatedTreatmentKidney, Polycystic1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b75ac0aede192dc2ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-4df9d81040eb8a48e65cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b8f9b479ca718fde6eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0290000000-88fa3da245399884b6bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-009e-0960000000-93c437b387d3e1aa7d90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-014i-0090000000-79e91c5055c98d8e3db0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-bdb88728428b2b7baa22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-9da9425656e26f3ca941View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-8c9267f9d7e631944de2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-c886ca3730f953370e44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-41f1d89cf454e5ae7574View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002b-0940000000-780c17885ad8db4f5a18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-2e61cf51b55f218dea78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ufr-0190000000-6c97fd1b1144abdb9fedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0umi-0190000000-fc4d25dd0d6b00a0dbc0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-7d7df50c05fdc5d6767aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-6dbcbd8581ffa5701094View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0101-2940000000-4b0a267fa20f8d45f167View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0590000000-c5a80156c2fb19e92afeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cd1368af6fd71ad45899View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-2f7fb214594d9dd58ff6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-106r-2090000000-9b129a417bc060d33cc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-48e785e66af8396f4347View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-2524a49c780104535532View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-2090000000-eb5ce4ed15fb44771926View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyanthraquinones. These are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassAnthracenes
Direct ParentHydroxyanthraquinones
Alternative ParentsAryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Polyols / Organic oxides / Hydrocarbon derivatives
SubstituentsHydroxyanthraquinone / Aryl ketone / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Vinylogous acid / Ketone / Polyol / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptorshydroxyanthraquinones (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 serine or threonine. Regulates numerous cellular processes, such as cell cycle progression, apoptosis and transcription, as well as viral infection. May act as a regulatory node which integrates and coor...
Gene Name:
CSNK2A1
Uniprot ID:
P68400
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
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 unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs (By similarity).
Gene Name:
fabZ
Uniprot ID:
Q5G940
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 (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and matu...
Gene Name:
AHR
Uniprot ID:
P35869
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 July 07, 2017 03:06