Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:57 UTC |
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Update date | 2019-11-26 03:09:11 UTC |
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Primary ID | FDB013862 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Emodin |
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Description | Emodin, 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. |
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CAS Number | 518-82-1 |
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Structure | |
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Synonyms | Synonym | Source |
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1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione | ChEBI | 1,3,8-Trihydroxy-6-methyl-9,10-anthraquinone | ChEBI | 3-METHYL-1,6,8-trihydroxyanthraquinone | ChEBI | Schuttgelb | ChEBI | 1,3, 8-Trihydroxy-6-methyl-9,10-anthraquinone | HMDB | 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9ci | HMDB | 1,3,8-Trihydroxy-6-methylanthra-9,10-quinone | HMDB | 4,5,7-Trihydroxy-2-methylanthraquinone | HMDB | 6-Methyl-1,3,8-trihydroxy-9,10-anthracenedione | HMDB | 6-Methyl-1,3,8-trihydroxyanthraquinone | HMDB | 9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9ci) | HMDB | Archin | HMDB, MeSH | Emodol | HMDB | Frangula emodin | HMDB, MeSH | Frangulic acid | HMDB, MeSH | Frangulinic acid | HMDB | Rheum-emodin | HMDB | Emodin, rheum | MeSH, HMDB | Emodin, frangula | MeSH, HMDB | Rheum emodin | MeSH, HMDB | 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9CI | db_source | 1,3,8-trihydroxy-6-methylanthra-9,10-quinone | biospider | 3-Methyl-1,6,8-trihydroxyanthraquinone | biospider | 6-methyl-1,3,8-trihydroxyanthraquinone | biospider | 9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9CI) | biospider | Alatinone | db_source | Emodin | db_source |
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Predicted Properties | |
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Chemical Formula | C15H10O5 |
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IUPAC name | 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione |
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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 |
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InChI Key | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O |
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Average Molecular Weight | 270.2369 |
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Monoisotopic Molecular Weight | 270.05282343 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Anthracenes |
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Sub Class | Anthraquinones |
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Direct Parent | Hydroxyanthraquinones |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 66.67%; H 3.73%; O 29.60% | DFC |
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Melting Point | Mp 266-268° (264-265°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 437 (e 12600) (EtOH) (Derep) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Emodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-007o-0590000000-e5d8430a10335839599b | Spectrum | Predicted GC-MS | Emodin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-2222900000-d6c47b3e4308e1f69c9d | Spectrum | Predicted GC-MS | Emodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-00di-0390000000-e186d58c552ffeba821e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00fr-2920000000-4cb1f49316cc48238122 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0090000000-7b75ac0aede192dc2ee6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0090000000-4df9d81040eb8a48e65c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0090000000-7b8f9b479ca718fde6ee | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-0290000000-88fa3da245399884b6bc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-009e-0960000000-93c437b387d3e1aa7d90 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-014i-0090000000-79e91c5055c98d8e3db0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0090000000-bdb88728428b2b7baa22 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0090000000-9da9425656e26f3ca941 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0090000000-8c9267f9d7e631944de2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0090000000-c886ca3730f953370e44 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0190000000-41f1d89cf454e5ae7574 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-002b-0940000000-780c17885ad8db4f5a18 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014i-0900000000-2e61cf51b55f218dea78 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0ufr-0190000000-6c97fd1b1144abdb9fed | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0umi-0190000000-fc4d25dd0d6b00a0dbc0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-05fr-1490000000-7d7df50c05fdc5d6767a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-05fr-1490000000-6dbcbd8581ffa5701094 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0090000000-cd1368af6fd71ad45899 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0090000000-2f7fb214594d9dd58ff6 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-106r-2090000000-9b129a417bc060d33cc1 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-48e785e66af8396f4347 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-2524a49c780104535532 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gdi-2090000000-eb5ce4ed15fb44771926 | 2015-04-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 3107 |
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ChEMBL ID | CHEMBL289277 |
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KEGG Compound ID | C10343 |
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Pubchem Compound ID | 3220 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 42223 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB07715 |
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HMDB ID | HMDB35214 |
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CRC / DFC (Dictionary of Food Compounds) ID | JJF10-F:JJF10-F |
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EAFUS ID | Not Available |
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Dr. Duke ID | EMODIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000555 |
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HET ID | EMO |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Emodin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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advanced glycation end products inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | aldose reductase inhibitor | 48550 | 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 | allergenic | 50904 | 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 aggregant | | | DUKE | anti angiogenic | 48422 | An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti cytomegalovirus | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti feedant | | | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti lymphomic | | | DUKE | anti methicillin-resistant Staphylococcus aureus | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti mutagenic | | | DUKE | anti neoplastic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti plaque | | | DUKE | anti proliferant | | | DUKE | anti sarcomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti sprout | | | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti ulcer | 49201 | 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 vaginitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | cathartic | 75325 | 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 depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | collagenase inhibitor | 23924 | 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 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | differentiator | | | DUKE | estrogenic | | | DUKE | genotoxic | 50902 | 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 | gonadotropic | | | DUKE | hypolipidemic | | | DUKE | immunostimulant | 50847 | 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 | immunosuppressant | 35705 | 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 inhibitor | 23924 | 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 | leucocytogenic | | | DUKE | matrix-metalloproteinase-2 inhibitor | 50664 | | DUKE | matrix-metalloproteinase-7 inhibitor | 50664 | | DUKE | matrix-metalloproteinase-9 inhibitor | 50664 | | DUKE | mutagenic | | | DUKE | nitric-oxide inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | pesticide | 25944 | 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 inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | protein kinase C inhibitor | 37700 | 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 inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | protein-tyrosine-kinase inhibitor | 23924 | 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 | purgative | 50503 | 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 | styptic | | | DUKE | topoisomerase-II inhibitor | 50750 | 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 | trichomonicide | | | DUKE | tyrosine-kinase inhibitor | 23924 | 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 | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE | vasorelaxant | | | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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