Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:29 UTC |
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Update date | 2020-02-24 19:10:36 UTC |
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Primary ID | FDB002708 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Juglone |
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Description | Juglone, also known as antibiotic PD7 or ci 75500, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Juglone is an extremely weak basic (essentially neutral) compound (based on its pKa). Juglone is found, on average, in the highest concentration within a few different foods, such as black walnuts, common walnuts, and liquors. Juglone has also been detected, but not quantified in, butternuts and nuts. This could make juglone a potential biomarker for the consumption of these foods. |
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CAS Number | 481-39-0 |
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Structure | |
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Synonyms | Synonym | Source |
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5-Hydroxy-1,4-naphthalenedione | ChEBI | 5-Hydroxy-1,4-naphthoquinone | ChEBI | 8-Hydroxy-1,4-naphthoquinone | ChEBI | -Hydroxy-1,4-naphthalenedione | HMDB | 5-Hydroxy-1,4-naphthalenedione, 9ci | HMDB | 8-Hydroxy-1,4-naphthalenedione | HMDB | Antibiotic PD7 | HMDB | C.I. natural brown 7 | HMDB | CI 75500 | HMDB | Lawsone | HMDB | Nucin | HMDB | PD7 | HMDB | Regianin | HMDB | 5-Hydroxy-1,4-naphthalenedione, 9CI | db_source | C.I. Natural Brown 7 | db_source | Juglone | db_source |
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Predicted Properties | |
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Chemical Formula | C10H6O3 |
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IUPAC name | 5-hydroxy-1,4-dihydronaphthalene-1,4-dione |
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InChI Identifier | InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H |
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InChI Key | KQPYUDDGWXQXHS-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=CC2=C1C(=O)C=CC2=O |
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Average Molecular Weight | 174.1528 |
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Monoisotopic Molecular Weight | 174.031694058 |
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Classification |
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Description | Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthoquinones |
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Direct Parent | Naphthoquinones |
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Alternative Parents | |
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Substituents | - Naphthoquinone
- Aryl ketone
- Quinone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Vinylogous acid
- Ketone
- 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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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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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 68.97%; H 3.47%; O 27.56% | DFC |
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Melting Point | Mp 155° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 1.92 | HANSCH,C ET AL. (1995) |
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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 | 422 (e 3630) (MeOH) | 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 | Juglone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dj-0900000000-fb8631f77002311df2c5 | Spectrum | Predicted GC-MS | Juglone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-5790000000-dfbf4959b881b9285503 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0006-0900000000-2fa9387180114c863fc4 | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-014i-0900000000-fefe993c0e30ef03165c | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-001i-0900000000-38ba61c5d0f8f05daf1e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-11e27d12e57f1d478761 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00b9-1900000000-3ba233f55939e221f9b0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00fr-9600000000-534e2b9919a0c9665a82 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-78b1f074f70ea780a1ef | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-78b1f074f70ea780a1ef | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dl-5900000000-22cd050139caaab81233 | Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 3674 |
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ChEMBL ID | CHEMBL43612 |
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KEGG Compound ID | C03840 |
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Pubchem Compound ID | 3806 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 652 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30773 |
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CRC / DFC (Dictionary of Food Compounds) ID | CND93-Z:CND93-Z |
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EAFUS ID | Not Available |
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Dr. Duke ID | JUGLONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000144 |
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HET ID | JUG |
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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 | Not Available |
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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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allelochemic | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti dermatophytic | | | DUKE | anti feedant | | | DUKE | anti parasitic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | dye | 37958 | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | keratolytic | | | 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 | quinone-reductase inducer | | | DUKE | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE | sternutatory | | | 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. — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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