Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-23 23:40:15 UTC |
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Update Date | 2021-09-23 23:40:15 UTC |
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HMDB ID | HMDB0303149 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Apigenin 7-O-beta-D-rutinoside |
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Description | Apigenin 7-o-beta-d-rutinoside, also known as rhoifolin or apigenin-7-O-rhamnoglucoside, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 7-o-beta-d-rutinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 7-o-beta-d-rutinoside can be found in carrot, orange mint, and wild carrot, which makes apigenin 7-o-beta-d-rutinoside a potential biomarker for the consumption of these food products. |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C27H30O14/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/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1 |
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Synonyms | Value | Source |
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7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one | ChEBI | Apigenin-7-O-rhamnoglucoside | ChEBI | Rhoifolin | ChEBI | Rhoifoloside | ChEBI | 7-((2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one | Generator | 7-((2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one | Generator | Apigenin 7-O-b-D-rutinoside | Generator | Apigenin 7-O-β-D-rutinoside | Generator |
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Chemical Formula | C27H30O14 |
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Average Molecular Weight | 578.5187 |
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Monoisotopic Molecular Weight | 578.163555668 |
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IUPAC Name | 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)-4H-chromen-4-one |
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Traditional Name | rhoifolin |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C27H30O14/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/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1 |
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InChI Key | RPMNUQRUHXIGHK-PYXJVEIZSA-N |
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Chemical Taxonomy |
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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
- Hydroxyflavonoid
- Flavone
- 5-hydroxyflavonoid
- 4'-hydroxyflavonoid
- Phenolic glycoside
- Chromone
- Glycosyl compound
- Disaccharide
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Phenol
- Monocyclic benzene moiety
- Oxane
- Benzenoid
- Pyran
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Primary alcohol
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF 40V, Negative-QTOF | splash10-002r-0905000000-7987816fb8648b0eea18 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF 10V, Negative-QTOF | splash10-002r-0905000000-7987816fb8648b0eea18 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF 20V, Negative-QTOF | splash10-002r-0905000000-7987816fb8648b0eea18 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF , Negative-QTOF | splash10-004i-0000092000-fe08120bacfe47df17f2 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF 30V, Negative-QTOF | splash10-004i-0000092000-fe08120bacfe47df17f2 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside ESI-TOF 40V, Negative-QTOF | splash10-004i-0000092000-fe08120bacfe47df17f2 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside LC-ESI-QFT 40V, positive-QTOF | splash10-001i-0000900000-0e57f1f59429661a74d1 | 2020-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside LC-ESI-IT 40V, positive-QTOF | splash10-00di-0090000000-99129ef4591876751de6 | 2020-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 10V, Positive-QTOF | splash10-00di-0290750000-55a6ae16cf519467ed4f | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 20V, Positive-QTOF | splash10-00di-0190300000-06d3ee053e5687568b07 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 40V, Positive-QTOF | splash10-00di-1390100000-f2c461f6351166e6fd45 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 10V, Negative-QTOF | splash10-02vi-4482980000-bf876ac84a2dcad10a60 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 20V, Negative-QTOF | splash10-014i-2591410000-6e87958379dbe1b68313 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 40V, Negative-QTOF | splash10-014i-6490000000-3ea18c33c05e3b5b5b90 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 10V, Positive-QTOF | splash10-00fr-0090040000-5360a5a561c2a6bbb4a8 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 20V, Positive-QTOF | splash10-00f0-0090910000-02c6a8c796e474e00fb9 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 40V, Positive-QTOF | splash10-00di-0090000000-60b322ff74af8a765580 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 10V, Negative-QTOF | splash10-004i-0000190000-48e73583084c06ab4561 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 20V, Negative-QTOF | splash10-00pi-0050790000-9b843f6502778be0c2e7 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Apigenin 7-O-beta-D-rutinoside 40V, Negative-QTOF | splash10-014i-0090010000-76c066300921436abb72 | 2021-10-21 | Wishart Lab | View Spectrum |
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