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 | FDB011866 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Naringin |
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Description | obtained from citrus fruits, Clymenia polyandra (clymenia) and Origanum vulgare (oregano)
Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavonone naringenin in humans. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro. Naringin is found in many foods, some of which are fruits, common sage, lime, and citrus. |
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CAS Number | 10236-47-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside] | ChEBI | Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside | ChEBI | Naringenin 7-O-neohesperidoside | ChEBI | Naringoside | ChEBI | Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside] | Generator | Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside] | Generator | Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucoside | Generator | Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucoside | Generator | 4'5-DiOH-flavone-7-rhgluc | HMDB | Naringin hydrate | HMDB | Nobiletin | HMDB | Naringenin-7-hesperidoside | HMDB | Naringin sodium | HMDB | Aurantiin | HMDB | 4',5,7-Trihydroxyflavanone 7-rhamnoglucoside | HMDB | Cyclorel | HMDB | Naringin dihydrochalcone | HMDB | Isohesperidin | db_source | Naringenin 7-neohesperidoside | db_source | Naringin | db_source |
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Predicted Properties | |
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Chemical Formula | C27H32O14 |
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IUPAC name | (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one |
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InChI Identifier | InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1 |
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InChI Key | DFPMSGMNTNDNHN-ZPHOTFPESA-N |
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Isomeric SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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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 fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acyl glycosides |
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Direct Parent | Fatty acyl glycosides of mono- and disaccharides |
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Alternative Parents | |
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Substituents | - Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty alcohol
- Sugar alcohol
- Oxane
- Secondary alcohol
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Liquid | |
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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 171° (dihydrate) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 1 mg/mL at 40 oC | MERCK INDEX (1996) |
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Experimental logP | -0.44 | PERRISSOUD,D & TESTA,B (1986) |
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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 | [a]19D -82.1 (EtOH) | DFC |
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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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GC-MS | Naringin, non-derivatized, GC-MS Spectrum | splash10-014j-0920000000-350bda4f263e4440e76a | Spectrum | GC-MS | Naringin, non-derivatized, GC-MS Spectrum | splash10-014j-0920000000-350bda4f263e4440e76a | Spectrum | Predicted GC-MS | Naringin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-044j-9521280000-3e3e40b7d28b4e903216 | Spectrum | Predicted GC-MS | Naringin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00ei-9302015000-e97b650a0d6a1b78ddc3 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0000090000-62ab85e8b85e9515ddc1 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negative | splash10-004i-0000091000-2671e4ecb91933035e78 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0100090000-0c16a31fd116a04809ff | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-00di-0290110000-a72cef11c1816469a269 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-00di-0290110000-a72cef11c1816469a269 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0000090000-d6285c4e4374990ed161 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0030290000-06238e4a98a4daad3265 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-004i-0030290000-06238e4a98a4daad3265 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0100090000-0c16a31fd116a04809ff | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-00di-0290110000-a72cef11c1816469a269 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0000090000-4498c4e102c3c7d3d514 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0000090000-d6285c4e4374990ed161 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0030290000-06238e4a98a4daad3265 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0fk9-0690000000-3d8f024f57318d3dbca8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0fk9-2981000000-e103705338e8e8855307 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00di-0290110000-a72cef11c1816469a269 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0000090000-4498c4e102c3c7d3d514 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0000090000-d6285c4e4374990ed161 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0030290000-06238e4a98a4daad3265 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00xr-0390740000-ed6375341eb1bebac319 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-0490200000-bbf5e62f8ba5ef5c55c6 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01b9-0940000000-043fddfc9269db83e1f1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-02or-3592880000-a3ec8e8504154578e09f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0229-2691310000-865585e62bd05144335b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-7590000000-82ba5c0120e07b81e87b | Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum | | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | | Spectrum |
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External Links |
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ChemSpider ID | 390868 |
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ChEMBL ID | CHEMBL451532 |
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KEGG Compound ID | C09789 |
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Pubchem Compound ID | 442428 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28819 |
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Phenol-Explorer ID | 208 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02927 |
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CRC / DFC (Dictionary of Food Compounds) ID | BFM77-B:HBH63-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | NARINGOSIDE|NARINGIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000983 |
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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 | Naringin |
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Phenol-Explorer Metabolite ID | 208 |
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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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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 | show |
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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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