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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:51 UTC
Update Date2019-07-23 06:18:04 UTC
HMDB IDHMDB0035214
Secondary Accession Numbers
  • HMDB35214
Metabolite Identification
Common NameEmodin
DescriptionEmodin, also known as schuttgelb or archin, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, emodin is considered to be an aromatic polyketide lipid molecule. It is an active ingredient of various Chinese herbs. Emodin is a drug. Emodin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, emodin has been detected, but not quantified in, a few different foods, such as docks, garden rhubarbs, and sorrels. This could make emodin a potential biomarker for the consumption of these foods. Emodin is a potentially toxic compound. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6.
Structure
Data?1563862684
Synonyms
ValueSource
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedioneChEBI
1,3,8-Trihydroxy-6-methyl-9,10-anthraquinoneChEBI
3-METHYL-1,6,8-trihydroxyanthraquinoneChEBI
SchuttgelbChEBI
1,3, 8-Trihydroxy-6-methyl-9,10-anthraquinoneHMDB
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9ciHMDB
1,3,8-Trihydroxy-6-methylanthra-9,10-quinoneHMDB
4,5,7-Trihydroxy-2-methylanthraquinoneHMDB
6-Methyl-1,3,8-trihydroxy-9,10-anthracenedioneHMDB
6-Methyl-1,3,8-trihydroxyanthraquinoneHMDB
9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9ci)HMDB
ArchinHMDB
EmodolHMDB
Frangula emodinHMDB
Frangulic acidHMDB
Frangulinic acidHMDB
Rheum-emodinHMDB
Emodin, rheumHMDB
Emodin, frangulaHMDB
Rheum emodinHMDB
Chemical FormulaC15H10O5
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Nameemodin
CAS Registry Number518-82-1
SMILES
CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O
InChI Identifier
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
InChI KeyRHMXXJGYXNZAPX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
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
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point266 - 268 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.13 m³·mol⁻¹ChemAxon
Polarizability26.58 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-0590000000-e5d8430a10335839599bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2222900000-d6c47b3e4308e1f69c9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0390000000-e186d58c552ffeba821eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00fr-2920000000-4cb1f49316cc48238122Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b75ac0aede192dc2ee6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-4df9d81040eb8a48e65cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b8f9b479ca718fde6eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0290000000-88fa3da245399884b6bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-009e-0960000000-93c437b387d3e1aa7d90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0090000000-79e91c5055c98d8e3db0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-bdb88728428b2b7baa22Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-9da9425656e26f3ca941Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-8c9267f9d7e631944de2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-c886ca3730f953370e44Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-41f1d89cf454e5ae7574Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002b-0940000000-780c17885ad8db4f5a18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-2e61cf51b55f218dea78Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ufr-0190000000-6c97fd1b1144abdb9fedSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0umi-0190000000-fc4d25dd0d6b00a0dbc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-7d7df50c05fdc5d6767aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-6dbcbd8581ffa5701094Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cd1368af6fd71ad45899Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-2f7fb214594d9dd58ff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-106r-2090000000-9b129a417bc060d33cc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-48e785e66af8396f4347Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-2524a49c780104535532Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-2090000000-eb5ce4ed15fb44771926Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07715
Phenol Explorer Compound IDNot Available
FooDB IDFDB013862
KNApSAcK IDC00000555
Chemspider ID3107
KEGG Compound IDC10343
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEmodin
METLIN IDNot Available
PubChem Compound3220
PDB IDNot Available
ChEBI ID42223
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Li HL, Chen HL, Li H, Zhang KL, Chen XY, Wang XW, Kong QY, Liu J: Regulatory effects of emodin on NF-kappaB activation and inflammatory cytokine expression in RAW 264.7 macrophages. Int J Mol Med. 2005 Jul;16(1):41-7. [PubMed:15942676 ]
  2. Sandholt IS, Olsen BB, Guerra B, Issinger OG: Resorufin: a lead for a new protein kinase CK2 inhibitor. Anticancer Drugs. 2009 Apr;20(4):238-48. doi: 10.1097/CAD.0b013e328326472e. [PubMed:19177021 ]
  3. Ubbink-Kok T, Anderson JA, Konings WN: Inhibition of electron transfer and uncoupling effects by emodin and emodinanthrone in Escherichia coli. Antimicrob Agents Chemother. 1986 Jul;30(1):147-51. [PubMed:3019234 ]
  4. Lee SU, Shin HK, Min YK, Kim SH: Emodin accelerates osteoblast differentiation through phosphatidylinositol 3-kinase activation and bone morphogenetic protein-2 gene expression. Int Immunopharmacol. 2008 May;8(5):741-7. doi: 10.1016/j.intimp.2008.01.027. Epub 2008 Feb 22. [PubMed:18387517 ]
  5. Kwak HJ, Park MJ, Park CM, Moon SI, Yoo DH, Lee HC, Lee SH, Kim MS, Lee HW, Shin WS, Park IC, Rhee CH, Hong SI: Emodin inhibits vascular endothelial growth factor-A-induced angiogenesis by blocking receptor-2 (KDR/Flk-1) phosphorylation. Int J Cancer. 2006 Jun 1;118(11):2711-20. [PubMed:16388516 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .