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',5,7-Trihydroxyflavanone 7-rhamnoglucoside | MeSH | Cyclorel | MeSH | Aurantiin | MeSH | Naringenin-7-hesperidoside | MeSH | Naringin dihydrochalcone | MeSH | Naringin sodium | MeSH | 4'5-DiOH-flavone-7-rhgluc | HMDB | Naringin hydrate | HMDB | Nobiletin | 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 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
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Oxane
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Secondary alcohol
- Ketone
- Polyol
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Ether
- Primary alcohol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- 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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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 | Predicted GC-MS | Naringin, "Naringin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Naringin, TMS_2_13, 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 - 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 | |
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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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