Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:40 UTC |
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Update date | 2020-02-24 19:10:12 UTC |
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Primary ID | FDB000683 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Nobiletin |
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Description | Nobiletin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, nobiletin is considered to be a flavonoid. Nobiletin is a bitter tasting compound. Nobiletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Nobiletin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits (Citrus X paradisi), lemons (Citrus limon), mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make nobiletin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nobiletin. |
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CAS Number | 478-01-3 |
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Structure | |
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Synonyms | Synonym | Source |
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5,6,7,8,3',4'-Hexamethoxyflavone | ChEBI | Hexamethoxyflavone | ChEBI | 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ci | HMDB | Flavone, 5,6,7,8,3',4'-hexamethoxy | HMDB | 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CI | db_source | Nobiletin | db_source |
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Predicted Properties | |
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Chemical Formula | C21H22O8 |
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IUPAC name | 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3 |
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InChI Key | MRIAQLRQZPPODS-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC |
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Average Molecular Weight | 402.3946 |
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Monoisotopic Molecular Weight | 402.13146768 |
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Classification |
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Description | Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | O-methylated flavonoids |
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Direct Parent | 8-O-methylated flavonoids |
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Alternative Parents | |
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Substituents | - 3p-methoxyflavonoid-skeleton
- 4p-methoxyflavonoid-skeleton
- 5-methoxyflavonoid-skeleton
- 6-methoxyflavonoid-skeleton
- 7-methoxyflavonoid-skeleton
- 8-methoxyflavonoid-skeleton
- Flavone
- Chromone
- Benzopyran
- O-dimethoxybenzene
- Dimethoxybenzene
- 1-benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Alkyl aryl ether
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Vinylogous ester
- Heteroaromatic compound
- Ether
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: |
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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 62.68%; H 5.51%; O 31.81% | DFC |
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Melting Point | Mp 134° | 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 | Not Available | |
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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 | Nobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dr-0109000000-1083a97d47bd665e7e3e | Spectrum | Predicted GC-MS | Nobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Nobiletin, 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 - LC-ESI-qTof , Positive | splash10-004i-0001900000-33c32e9e66704097c76a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00kb-4930000000-6905f538e3d50304566b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-06rf-0039000000-1f10f3c85ebc9576e9e8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-ec4f0760bcd6e1c1fcec | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-a07fe56ebf7850515513 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-00dr-0009000000-f517eba98f7a9c2ef6dc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-26380311919f21cc1264 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-a1ea51facc9a617005d9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-ed668e0372bef20e7e1e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0003900000-abbce9b6fc298b405ea6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0uki-0009600000-6e113107c7038d9754bf | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0079-0009000000-c7bb5f00231de5038448 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0017900000-76a74f58aaa8107742e6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-004i-0001900000-33c32e9e66704097c76a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00di-1449000000-515986740b5064496d80 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0001900000-27af360ec486a6c3d9c3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0fki-0009200000-4319c91ac3c4b550666e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0uk9-0009700000-3eec55e1b3cc7eef561a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0129000000-56a5cc483729ca41cd8c | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000900000-4cb76fd70e9da24d2d79 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0001900000-1e46aabd07d48fdf1812 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02ml-0249000000-571e1067224eee352140 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000900000-7349cf45f0a975c8fa0d | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0006900000-635ddb31cf10fc1ba687 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06rl-0169000000-608732c8f7b6ff235974 | 2015-04-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 65283 |
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ChEMBL ID | CHEMBL76447 |
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KEGG Compound ID | C10112 |
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Pubchem Compound ID | 72344 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 237 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB29540 |
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CRC / DFC (Dictionary of Food Compounds) ID | BFN32-P:BFN32-P |
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EAFUS ID | Not Available |
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Dr. Duke ID | NOBILETIN|NOBELITIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001076 |
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HET ID | Not Available |
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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 | Nobiletin |
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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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Anti-allergic | 50857 | An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies. | DUKE | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | DUKE | Anti-proliferative | | An agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Cholinergic | 38323 | An agent that stimulates the parasympathetic nervous system by mimicking acetylcholine, enhancing muscle contraction, and regulating various bodily functions. Therapeutically, it treats conditions like glaucoma, myasthenia gravis, and Alzheimer's disease, improving muscle tone, cognition, and eye pressure. | DUKE | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | Fungistat | | An agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | 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 | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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). — 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. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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