Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:26 UTC |
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Update date | 2019-11-26 02:57:40 UTC |
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Primary ID | FDB002597 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cyanidin 3,5-diglucoside |
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Description | Cyanidin 3,5-diglucoside belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Cyanidin 3,5-diglucoside is found, on average, in the highest concentration within a few different foods, such as white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.), cabbages (Brassica oleracea var. capitata), and black elderberries (Sambucus nigra) and in a lower concentration in pomegranates (Punica granatum) and common beans (Phaseolus vulgaris). Cyanidin 3,5-diglucoside has also been detected, but not quantified in, several different foods, such as garden onions (Allium cepa), redcurrants (Ribes rubrum), chives (Allium schoenoprasum), malus (crab apple), and grapes (Vitis). This could make cyanidin 3,5-diglucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3,5-diglucoside. |
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CAS Number | 2611-67-8 |
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Structure | |
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Synonyms | Synonym | Source |
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Cyanenin | db_source | Cyanidin 3,5-diglucoside | db_source | Cyanin | db_source | Shisonin A | db_source |
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Predicted Properties | |
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Chemical Formula | C27H31O16 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium |
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InChI Identifier | InChI=1S/C27H30O16/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32)/p+1/t17?,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1 |
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InChI Key | RDFLLVCQYHQOBU-QZTFBGFRSA-O |
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Isomeric SMILES | OC[C@H]1O[C@@H](OC2=CC3=C(O[C@@H]4OC(CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 611.5254 |
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Monoisotopic Molecular Weight | 611.161209944 |
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Classification |
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Description | Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-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 | Anthocyanidin-5-O-glycosides |
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Alternative Parents | |
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Substituents | - Anthocyanidin-5-o-glycoside
- Anthocyanidin-3-o-glycoside
- Flavonoid-3-o-glycoside
- Hydroxyflavonoid
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- Anthocyanidin
- Phenolic glycoside
- O-glycosyl compound
- Glycosyl compound
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Organic cation
- 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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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 53.03%; H 5.11%; O 41.86% | DFC |
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Melting Point | Mp 203-204° (chloride) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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]D -258 (HCl aq.) | 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 | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0100009000-b715f4da249bc24ca679 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06r6-2600089000-9918cc8163362e7fa600 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dm-6900130000-d067f93d7b9c9925623b | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1200009000-8ba97a109b647725d1d3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fr-5700019000-2dafd8cdc16bb9acf2b4 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100200000-a1b33d50ed6fc0682daa | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 441688 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 3978 |
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Phenol-Explorer ID | 71 |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | ODW40-I:CMQ11-F |
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EAFUS ID | Not Available |
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Dr. Duke ID | CYANIDIN-3,5-DI-O-GLUCOSIDE|CYANIDIN-3,5-DIGLUCOSIDE|CYANIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002378 |
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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 | Not Available |
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Phenol-Explorer Metabolite ID | 71 |
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Duplicate IDS | Not Available |
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Old DFC IDS | CMQ73-Z:CMQ11-F |
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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 | Descriptor | ID | Definition | Reference |
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anti polio | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | emetic | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | pigment | 26130 | An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light. | DUKE |
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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 | Not Available |
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Files |
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MSDS | Not Available |
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — 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.
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