Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2018-05-29 01:08:20 UTC
Primary IDFDB013862
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEmodin
DescriptionPresent in Cascara sagrada Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. Emodin is found in dock, garden rhubarb, and sorrel.
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
EmodolHMDB
Frangula emodinHMDB
Frangulic acidHMDB
Frangulinic acidHMDB
Rheum-emodinHMDB
Emodin, rheumHMDB
Emodin, frangulaHMDB
Rheum emodinHMDB
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-0590000000-e5d8430a10335839599bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2222900000-d6c47b3e4308e1f69c9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0390000000-e186d58c552ffeba821eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00fr-2920000000-4cb1f49316cc48238122View in MoNA
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-ITFT , 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
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
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
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.