Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:52 UTC |
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Update date | 2019-11-26 03:05:37 UTC |
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Primary ID | FDB011868 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Narirutin |
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Description | Narirutin belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Narirutin is a bland tasting compound. Narirutin is found, on average, in the highest concentration within a few different foods, such as peppermints (Mentha X piperita), grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima), and grapefruits (Citrus X paradisi) and in a lower concentration in mandarin orange (clementine, tangerine), lemons (Citrus limon), and sweet oranges (Citrus sinensis). Narirutin has also been detected, but not quantified in, several different foods, such as green tea, fruit juice, teas (Camellia sinensis), black tea, and red tea. This could make narirutin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Narirutin. |
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CAS Number | 14259-46-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Isonaringenin | HMDB | Isonaringin | HMDB | Naringenin 7-O-rutinoside | HMDB | Naringenin 7-rutinoside | HMDB | Narirutin | db_source |
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Predicted Properties | |
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Chemical Formula | C27H32O14 |
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IUPAC name | 5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2H-1-benzopyran-4-one |
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InChI Identifier | InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3 |
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InChI Key | HXTFHSYLYXVTHC-UHFFFAOYSA-N |
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Isomeric SMILES | CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)CC(OC4=C3)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(O)C1O |
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Average Molecular Weight | 580.5346 |
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Monoisotopic Molecular Weight | 580.179205732 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. |
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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 | Flavonoid glycosides |
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Direct Parent | Flavonoid-7-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-7-o-glycoside
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavanone
- Hydroxyflavonoid
- Flavan
- Phenolic glycoside
- Chromone
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Chromane
- Benzopyran
- 1-benzopyran
- Aryl alkyl ketone
- Aryl ketone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Oxane
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Secondary alcohol
- Ketone
- Polyol
- Acetal
- Organoheterocyclic compound
- Ether
- Oxacycle
- Alcohol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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: Source: Biological location: |
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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 55.86%; H 5.56%; O 38.58% | DFC |
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Melting Point | Mp 160-165° | 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 | Narirutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-08g0-6491080000-bfc7de611c3013f304b8 | Spectrum | Predicted GC-MS | Narirutin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052r-6573019000-4ba17bdd65d032ee9461 | Spectrum | Predicted GC-MS | Narirutin, "Narirutin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Narirutin, TMS_2_15, 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 - 6V, Positive | splash10-00di-0190020000-72e87039bd196ece89f5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0390000000-5334b9b29d5ffc2524c6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0040090000-0fbae62ef6d382014ee1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0uxr-0900000000-bc72835c13c53afbc76e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0uxr-0900000000-4eae0b084f561b38e812 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0uxr-0900000000-04cac72da4eecb94d5b2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0390000000-f170ea1a494bb4b8f19f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0390000000-1cf0b9714da8b9af8abd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0292310000-108c4ab7874923027549 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0190020000-1d9bec3316e4f7320988 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0030090000-3be8ed23845b4a2deac3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0030090000-5f3f2e9ccf23e42d69e9 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-00di-0190020000-936ce764ebc32f2b12a1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00di-0292310000-62a72694f8207091b2fc | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0229-0290260000-98c3442451abc4367b35 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-0490100000-8fdbeb4bd4a89e54c594 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0960000000-9f8dbd08c6aaa4692c39 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0200-4390380000-2cef0927ada9091c03a0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-3590020000-8fe4efb7aac2b262964a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-3590000000-ecd5801ef9665c7489e0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0030090000-126fb6fa79bb7a288c76 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fr-0190070000-c4c64ba704b3186390e8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fk9-0970020000-3928c9310ebd1a87e631 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00e9-0080950000-28cd744c41ec3389c0d2 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0190200000-78e12ac965ab32f2aef4 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 77296 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09793 |
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Pubchem Compound ID | 85704 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28705 |
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Phenol-Explorer ID | 209 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB33740 |
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CRC / DFC (Dictionary of Food Compounds) ID | BFM77-B:HBH89-T |
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EAFUS ID | Not Available |
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Dr. Duke ID | NARIRUTIN|NARINGIN-7-O-ALPHA-L-RHAMNO-GLUCOSIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000984 |
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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 | rw1057341 |
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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 | |
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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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bland |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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 | — 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. — 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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