Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:51 UTC
Update Date2022-03-07 02:54:24 UTC
HMDB IDHMDB0035214
Secondary Accession Numbers
  • HMDB35214
Metabolite Identification
Common 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. Emodin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Emodin.
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, MeSH
EmodolHMDB
Frangula emodinHMDB, MeSH
Frangulic acidHMDB, MeSH
Frangulinic acidHMDB
Rheum-emodinHMDB
Emodin, rheumMeSH, HMDB
Emodin, frangulaMeSH, HMDB
Rheum emodinMeSH, HMDB
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
Disposition
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point266 - 268 °CNot Available
Boiling Point586.87 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.04 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.641 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker156.90630932474
[M+H]+Baker161.29630932474
[M-H]-Not Available156.906http://allccs.zhulab.cn/database/detail?ID=AllCCS00001921
[M+H]+Not Available161.296http://allccs.zhulab.cn/database/detail?ID=AllCCS00001921
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.07131661259
DarkChem[M-H]-163.35631661259
DeepCCS[M+H]+162.50230932474
DeepCCS[M-H]-160.14430932474
DeepCCS[M-2H]-193.59830932474
DeepCCS[M+Na]+168.82530932474
AllCCS[M+H]+159.532859911
AllCCS[M+H-H2O]+155.732859911
AllCCS[M+NH4]+163.132859911
AllCCS[M+Na]+164.132859911
AllCCS[M-H]-161.132859911
AllCCS[M+Na-2H]-160.332859911
AllCCS[M+HCOO]-159.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EmodinCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O3839.8Standard polar33892256
EmodinCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O2384.0Standard non polar33892256
EmodinCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O2782.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Emodin,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C12631.4Semi standard non polar33892256
Emodin,1TMS,isomer #2CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C12733.4Semi standard non polar33892256
Emodin,1TMS,isomer #3CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C(=O)C2=C12614.8Semi standard non polar33892256
Emodin,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C12683.3Semi standard non polar33892256
Emodin,2TMS,isomer #2CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C(=O)C2=C12629.4Semi standard non polar33892256
Emodin,2TMS,isomer #3CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C12664.7Semi standard non polar33892256
Emodin,3TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C12676.4Semi standard non polar33892256
Emodin,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C12892.3Semi standard non polar33892256
Emodin,1TBDMS,isomer #2CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C12980.4Semi standard non polar33892256
Emodin,1TBDMS,isomer #3CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C(=O)C2=C12879.1Semi standard non polar33892256
Emodin,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C13175.6Semi standard non polar33892256
Emodin,2TBDMS,isomer #2CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C(=O)C2=C13128.0Semi standard non polar33892256
Emodin,2TBDMS,isomer #3CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C13154.7Semi standard non polar33892256
Emodin,3TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C13346.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Emodin GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-0590000000-e5d8430a10335839599b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emodin GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2222900000-d6c47b3e4308e1f69c9d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emodin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin DI-ESI-qTof , Positive-QTOFsplash10-00di-0390000000-e186d58c552ffeba821e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-qTof , Positive-QTOFsplash10-00fr-2920000000-4cb1f49316cc482381222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-7b75ac0aede192dc2ee62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-4df9d81040eb8a48e65c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-7b8f9b479ca718fde6ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , negative-QTOFsplash10-004i-0290000000-88fa3da245399884b6bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , negative-QTOFsplash10-009e-0960000000-93c437b387d3e1aa7d902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-ITFT , negative-QTOFsplash10-014i-0090000000-79e91c5055c98d8e3db02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , negative-QTOFsplash10-004i-0090000000-bdb88728428b2b7baa222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , negative-QTOFsplash10-004i-0090000000-9da9425656e26f3ca9412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , positive-QTOFsplash10-00di-0090000000-8c9267f9d7e631944de22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , positive-QTOFsplash10-00di-0090000000-c886ca3730f953370e442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , positive-QTOFsplash10-00di-0190000000-41f1d89cf454e5ae75742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , positive-QTOFsplash10-002b-0940000000-780c17885ad8db4f5a182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-2e61cf51b55f218dea782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , positive-QTOFsplash10-0ufr-0190000000-6c97fd1b1144abdb9fed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , positive-QTOFsplash10-0umi-0190000000-fc4d25dd0d6b00a0dbc02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , positive-QTOFsplash10-05fr-1490000000-7d7df50c05fdc5d6767a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Emodin Linear Ion Trap , positive-QTOFsplash10-05fr-1490000000-6dbcbd8581ffa57010942017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 10V, Positive-QTOFsplash10-00di-0090000000-cd1368af6fd71ad458992015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 20V, Positive-QTOFsplash10-00di-0090000000-2f7fb214594d9dd58ff62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 40V, Positive-QTOFsplash10-106r-2090000000-9b129a417bc060d33cc12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 10V, Negative-QTOFsplash10-014i-0090000000-48e785e66af8396f43472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 20V, Negative-QTOFsplash10-014i-0090000000-2524a49c7801045355322015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emodin 40V, Negative-QTOFsplash10-0gdi-2090000000-eb5ce4ed15fb447719262015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1242531
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.. .