Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2019-11-26 03:09:11 UTC
Primary IDFDB013862
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEmodin
DescriptionEmodin, also known as schuttgelb, 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. Emodin has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and sorrels (Rumex acetosa). This could make emodin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Emodin.
CAS Number518-82-1
Structure
Thumb
Synonyms
SynonymSource
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, MeSH
EmodolHMDB
Frangula emodinHMDB, MeSH
Frangulic acidHMDB, MeSH
Frangulinic acidHMDB
Rheum-emodinHMDB
Emodin, rheumMeSH, HMDB
Emodin, frangulaMeSH, HMDB
Rheum emodinMeSH, HMDB
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9CIdb_source
1,3,8-trihydroxy-6-methylanthra-9,10-quinonebiospider
3-Methyl-1,6,8-trihydroxyanthraquinonebiospider
6-methyl-1,3,8-trihydroxyanthraquinonebiospider
9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9CI)biospider
Alatinonedb_source
Emodindb_source
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
Chemical FormulaC15H10O5
IUPAC name1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione
InChI IdentifierInChI=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
Isomeric SMILESCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 266-268° (264-265°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data437 (e 12600) (EtOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEmodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007o-0590000000-e5d8430a10335839599bSpectrum
Predicted GC-MSEmodin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2222900000-d6c47b3e4308e1f69c9dSpectrum
Predicted GC-MSEmodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0390000000-e186d58c552ffeba821e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00fr-2920000000-4cb1f49316cc482381222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b75ac0aede192dc2ee62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-4df9d81040eb8a48e65c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-7b8f9b479ca718fde6ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0290000000-88fa3da245399884b6bc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-009e-0960000000-93c437b387d3e1aa7d902017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0090000000-79e91c5055c98d8e3db02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-bdb88728428b2b7baa222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0090000000-9da9425656e26f3ca9412017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-8c9267f9d7e631944de22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-c886ca3730f953370e442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-41f1d89cf454e5ae75742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002b-0940000000-780c17885ad8db4f5a182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-2e61cf51b55f218dea782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ufr-0190000000-6c97fd1b1144abdb9fed2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0umi-0190000000-fc4d25dd0d6b00a0dbc02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-7d7df50c05fdc5d6767a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05fr-1490000000-6dbcbd8581ffa57010942017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cd1368af6fd71ad458992015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-2f7fb214594d9dd58ff62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-106r-2090000000-9b129a417bc060d33cc12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-48e785e66af8396f43472015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-2524a49c7801045355322015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-2090000000-eb5ce4ed15fb447719262015-04-25View Spectrum
NMRNot Available
ChemSpider ID3107
ChEMBL IDCHEMBL289277
KEGG Compound IDC10343
Pubchem Compound ID3220
Pubchem Substance IDNot Available
ChEBI ID42223
Phenol-Explorer IDNot Available
DrugBank IDDB07715
HMDB IDHMDB35214
CRC / DFC (Dictionary of Food Compounds) IDJJF10-F:JJF10-F
EAFUS IDNot Available
Dr. Duke IDEMODIN
BIGG IDNot Available
KNApSAcK IDC00000555
HET IDEMO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEmodin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
advanced glycation end products inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti aggregantDUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cytomegalovirus22587 A substance that destroys or inhibits replication of viruses.DUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lymphomicDUKE
anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.DUKE
anti mutagenicDUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti plaqueDUKE
anti proliferantDUKE
anti sarcomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti sproutDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti vaginitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cathartic75325 Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
collagenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
differentiatorDUKE
estrogenicDUKE
genotoxic50902 A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.DUKE
gonadotropicDUKE
hypolipidemicDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
iNOS inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
leucocytogenicDUKE
matrix-metalloproteinase-2 inhibitor50664 DUKE
matrix-metalloproteinase-7 inhibitor50664 DUKE
matrix-metalloproteinase-9 inhibitor50664 DUKE
mutagenicDUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin-E2 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
purgative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
stypticDUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
trichomonicideDUKE
tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vasorelaxantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.