Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:53:43 UTC |
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Update Date | 2022-03-07 02:53:35 UTC |
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HMDB ID | HMDB0033098 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside |
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Description | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside has been detected, but not quantified in, fruits. This could make 5,7-dihydroxy-6-methoxyflavone 5-rhamnoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside. |
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Structure | COC1=C(OC2OC(C)C(O)C(O)C2O)C2=C(OC(=CC2=O)C2=CC=CC=C2)C=C1O InChI=1S/C22H22O9/c1-10-17(25)18(26)19(27)22(29-10)31-21-16-12(23)8-14(11-6-4-3-5-7-11)30-15(16)9-13(24)20(21)28-2/h3-10,17-19,22,24-27H,1-2H3 |
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Synonyms | Not Available |
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Chemical Formula | C22H22O9 |
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Average Molecular Weight | 430.4047 |
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Monoisotopic Molecular Weight | 430.126382302 |
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IUPAC Name | 7-hydroxy-6-methoxy-2-phenyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one |
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Traditional Name | 7-hydroxy-6-methoxy-2-phenyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one |
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CAS Registry Number | 163350-29-6 |
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SMILES | COC1=C(OC2OC(C)C(O)C(O)C2O)C2=C(OC(=CC2=O)C2=CC=CC=C2)C=C1O |
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InChI Identifier | InChI=1S/C22H22O9/c1-10-17(25)18(26)19(27)22(29-10)31-21-16-12(23)8-14(11-6-4-3-5-7-11)30-15(16)9-13(24)20(21)28-2/h3-10,17-19,22,24-27H,1-2H3 |
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InChI Key | NNXFUYOQDUBSHH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one 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 | Flavonoid glycosides |
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Direct Parent | Flavonoid O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-5-o-glycoside
- Flavonoid o-glycoside
- 6-methoxyflavonoid-skeleton
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Phenolic glycoside
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Anisole
- Pyranone
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Pyran
- Oxane
- Monocyclic benzene moiety
- Monosaccharide
- Benzenoid
- Vinylogous ester
- Heteroaromatic compound
- Secondary alcohol
- Ether
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Polyol
- Organooxygen compound
- Organic oxide
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 327 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TMS,isomer #1 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O)C1O | 3756.9 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TMS,isomer #2 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C)C1O | 3746.7 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O[Si](C)(C)C | 3727.5 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O | 3824.9 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O)C1O | 3712.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #2 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 3616.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 3611.5 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C)C1O | 3703.0 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #5 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3610.2 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TMS,isomer #6 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O[Si](C)(C)C | 3677.8 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 3638.8 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TMS,isomer #2 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 3617.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3563.6 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3619.0 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,4TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3608.4 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TBDMS,isomer #1 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 4001.2 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TBDMS,isomer #2 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 3990.2 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TBDMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 3979.7 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,1TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O | 4047.9 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 4168.6 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #2 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 4094.4 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 4086.6 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 4164.2 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #5 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4098.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,2TBDMS,isomer #6 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 4133.0 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 4272.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 4239.9 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TBDMS,isomer #3 | COC1=C(O)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4212.0 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,3TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4242.1 | Semi standard non polar | 33892256 | 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside,4TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)=CC(=O)C2=C1OC1OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4408.0 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside GC-MS (Non-derivatized) - 70eV, Positive | splash10-0bt9-9103300000-3cbbfc0396d52c0f9feb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside GC-MS (3 TMS) - 70eV, Positive | splash10-001i-4552019000-37f4fe401263d43c6864 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 10V, Positive-QTOF | splash10-0019-0090700000-eda85073118de244b48f | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 20V, Positive-QTOF | splash10-000i-0090000000-6b65d6421f2181e786f5 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 40V, Positive-QTOF | splash10-00kr-2390000000-493f36ffa11cc78e9255 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 10V, Negative-QTOF | splash10-0059-1052900000-fd8e16d7563c2af1ec7d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 20V, Negative-QTOF | splash10-00lr-1091100000-29ebbcd019eca5c799a8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 40V, Negative-QTOF | splash10-02u0-1190000000-bff4f02c49a7cb8448cd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 10V, Negative-QTOF | splash10-004i-0000900000-472afde216effb41d5dd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 20V, Negative-QTOF | splash10-004i-0000900000-99c8ca0f815ae9ee09c4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 40V, Negative-QTOF | splash10-002f-0925200000-d3d1ef72acbb5ebe9efc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 10V, Positive-QTOF | splash10-001i-0000900000-ef3d3b83667d3d38ca3f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 20V, Positive-QTOF | splash10-001i-0000900000-ef3d3b83667d3d38ca3f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-6-methoxyflavone 5-rhamnoside 40V, Positive-QTOF | splash10-003r-0119600000-990219a1dc266244fe4c | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011093 |
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KNApSAcK ID | C00004483 |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 74977829 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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