Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:53:37 UTC |
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Updated at | 2020-11-18 16:39:05 UTC |
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CannabisDB ID | CDB004949 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Rutin |
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Description | Rutin, also known as rutoside or phytomelin, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Rutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Rutin is found, on average, in the highest concentration within a few different foods, such as parsley, common buckwheats, and sorrels and in a lower concentration in grape wines, italian sweet red peppers, and nectarines. Rutin has also been detected, but not quantified in, several different foods, such as summer grapes, peachs, broccoli, rosemaries, and tartary buckwheats. This could make rutin a potential biomarker for the consumption of these foods. A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. Rutin is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | ChEBI | 3-Rhamnoglucosylquercetin | ChEBI | 3-Rutinosyl quercetin | ChEBI | Phytomelin | ChEBI | Quercetin 3-rutinoside | ChEBI | Quercetin-3-rutinoside | ChEBI | Rutoside | ChEBI | Venoruton | Kegg | 3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | Generator | 3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | Generator | 3-Rhamnosyl-glucosyl quercetin | MeSH | Quercetin 3 rutinoside | MeSH | Quercetin, 3-rhamnosyl-glucosyl | MeSH | 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside | HMDB | 3-Rhamnoglucoside OF 3,3',4',5,7-pentahydroxyflavone | HMDB | beta-Quercetin-3-rutinoside | HMDB | Bioflavonoid | HMDB | Birutan | HMDB | Birutan forte | HMDB | Birutin | HMDB | Eldrin | HMDB | Globulariacitrin | HMDB | Globularicitrin | HMDB | Ilixanthin | HMDB | Melin | HMDB | Myrticolorin | HMDB | Neoisorutin | HMDB | Osyritrin | HMDB | Oxyritin | HMDB | Paliuroside | HMDB | Quercetin 3-O-beta-D-rutinoside | HMDB | Quercetin 3-O-beta-delta-rutinoside | HMDB | Quercetin 3-O-rutinoside | HMDB | Quercetin 3-rhamnoglucoside | HMDB | Quercetin rhamnoglucosine | HMDB | Quercetin-3beta-rutinoside | HMDB | Quercetol 3-rhamnoglucoside | HMDB | Quercitin 3-rutinoside | HMDB | RUT | HMDB | Rutabion | HMDB | Rutin trihydrate | HMDB | Rutine | HMDB | Rutinic acid | HMDB | Rutinion acid | HMDB | Rutinum | HMDB | Rutosid | HMDB | Rutosido | HMDB | Rutosidum | HMDB | Rutozyd | HMDB | Sophorin | HMDB | Tanrutin | HMDB | Violaquercitrin | HMDB | Vitamin P | HMDB | Rutin | KEGG | 3,3',4',5,7-Pentahydroxyflavone 3-O-rutinoside | PhytoBank | 3,3’,4’,5,7-Pentahydroxyflavone 3-O-rutinoside | PhytoBank | 3,3',4',5,7-Pentahydroxyflavone 3-rutinoside | PhytoBank | 3,3’,4’,5,7-Pentahydroxyflavone 3-rutinoside | PhytoBank | 3-O-Rutinosylquercetin | PhytoBank | 3-Rutinosylquercetin | PhytoBank | 5,7,3',4'-Tetrahydroxyflavonol-3-O-rutinoside | PhytoBank | 5,7,3’,4’-Tetrahydroxyflavonol-3-O-rutinoside | PhytoBank | Ilixathin | PhytoBank | Myrticalorin | PhytoBank | Myticolorin | PhytoBank | Quercetin 3-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside) | PhytoBank | Quercetin 3-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside) | PhytoBank | Quercetin 6-O-alpha-L-rhamnosyl-beta-D-glucoside | PhytoBank | Quercetin 6-O-α-L-rhamnosyl-β-D-glucoside | PhytoBank | Quercetin-3-O-[alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside] | PhytoBank | Quercetin-3-O-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] | PhytoBank | Quercetin 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside | PhytoBank | Quercetin 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside | PhytoBank | Quercetin 3-O-α-L-rhamnopyranosyl-β-D-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl(1''->6')-beta-D-glucopyranoside | PhytoBank | Quercetin 3-O-α-rhamnopyranosyl(1''→6')-β-D-glucopyranoside | PhytoBank | Quercetin 3-O-α-rhamnopyranosyl(1’’→6’)-β-D-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl(1->6)-beta-glucopyranoside | PhytoBank | Quercetin 3-O-α-rhamnopyranosyl(1→6)-β-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl-(1'''->6'')-beta-glucopyranoside | PhytoBank | Quercetin 3-O-α-rhamnopyranosyl-(1'''→6'')-β-glucopyranoside | PhytoBank | Quercetin 3-O-α-rhamnopyranosyl-(1’’’→6’’)-β-glucopyranoside | PhytoBank | Quercetin 3-O-beta-D-(6''-O-alpha-L-rhamnopyranosyl)glucopyranoside | PhytoBank | Quercetin 3-O-β-D-(6''-O-α-L-rhamnopyranosyl)glucopyranoside | PhytoBank | Quercetin 3-O-β-D-(6’’-O-α-L-rhamnopyranosyl)glucopyranoside | PhytoBank | Quercetin 3-O-β-D-rutinoside | PhytoBank | Quercetin 3-O-beta-rutinoside | PhytoBank | Quercetin 3-O-β-rutinoside | PhytoBank | Quercetin 3-beta-rutinoside | PhytoBank | Quercetin 3-β-rutinoside | PhytoBank | Quercetin-3-O-[alpha-L-rhamnopyranosyl-(1→6)-beta-D-glucopyranoside] | PhytoBank | Quercetin 3-O-alpha-L-rhamnopyranosyl-(1→6)-beta-D-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl(1''→6')-beta-D-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl(1→6)-beta-glucopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnopyranosyl-(1'''→6'')-beta-glucopyranoside | PhytoBank | Quercetin rutinoside | PhytoBank | Rutozid | PhytoBank | Violaquercetrin | PhytoBank |
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Chemical Formula | C27H30O16 |
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Average Molecular Weight | 610.52 |
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Monoisotopic Molecular Weight | 610.1534 |
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IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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Traditional Name | troxerutin |
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CAS Registry Number | 153-18-4 |
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SMILES | C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1 |
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InChI Key | IKGXIBQEEMLURG-NVPNHPEKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-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-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- Hydroxyflavonoid
- Flavone
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Chromone
- 1-benzopyran
- Benzopyran
- Catechol
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Oxane
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Polyol
- Organic oxide
- Organic oxygen compound
- Alcohol
- 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: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 125 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.12 mg/mL | Not Available | logP | Not Available | Not Available |
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Predicted Properties | [] |
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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 | Rutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052p-7581190000-d9593c696e6c6e2454ed | Spectrum | Predicted GC-MS | Rutin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Rutin, TMS_2_14, 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) | splash10-03di-0000009000-a6b8403579a83c69506b | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-0002009000-ffacf122369038644c02 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0w29-5009015000-f74826ba5205775d12b8 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-03di-0003109000-85542c3510756d258e11 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive | splash10-0ik9-0008109000-f0d08078ad4b887cce0d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0a4i-0000009000-f07697affe03ff93dad3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive | splash10-0udi-0009000000-1b117e308c1ab00aa4a7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0000009000-270308e3f77a0404dea8 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0010009000-f94b0edacf4c3bc9c9e3 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0udi-0049001000-8327d9d15b0d22a0c968 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0000009000-270308e3f77a0404dea8 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0010009000-f94b0edacf4c3bc9c9e3 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0udi-0049001000-8327d9d15b0d22a0c968 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0udi-0009100000-dfc0a2b72193a5072dde | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0000009000-dd163a2a17fe559c3482 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0000009000-7b408d31853f85c12619 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0001009000-3a559cbd175dfd7bafc9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0009005000-a090fd87b44b66b9f0c0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0009000000-8454cc7afaccaa2be7ac | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0139143000-0b231bbaf0f8cd578ce9 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0249200000-5766b78c90749219634c | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udr-1955000000-49ac7b74c557179bbcae | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0pb9-5539337000-13a750c25d00b7185c08 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-3539010000-707593795636ef3841c1 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-3966000000-61676ecb8f5b5e514760 | 2017-07-26 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | |
Aldo-keto reductase family 1 member C3 | AKR1C3 | 10p15-p14 | P42330 | details |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | |
Aldo-keto reductase family 1 member C3 | AKR1C3 | 10p15-p14 | P42330 | details |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0003249 |
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DrugBank ID | DB01698 |
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Phenol Explorer Compound ID | 296 |
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FoodDB ID | FDB002536 |
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KNApSAcK ID | C00005413 |
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Chemspider ID | 4444362 |
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KEGG Compound ID | C05625 |
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BioCyc ID | RUTIN |
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BiGG ID | Not Available |
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Wikipedia Link | Rutin |
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METLIN ID | 3677 |
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PubChem Compound | 5280805 |
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PDB ID | Not Available |
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ChEBI ID | 28527 |
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References |
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General References | Not Available |
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