| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:24 UTC |
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| Update date | 2019-11-26 02:54:29 UTC |
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| Primary ID | FDB000035 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Peonidin 3-(6''-p-coumaroyl-glucoside) |
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| Description | Peonidin 3-(6''-p-coumaroyl-glucoside) is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Peonidin 3-(6''-p-coumaroyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-(6''-p-coumaroyl-glucoside) can be found in common grape and grape wine, which makes peonidin 3-(6''-p-coumaroyl-glucoside) a potential biomarker for the consumption of these food products. |
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| CAS Number | 147-85-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Peonidin 3-O-(6''-p-coumaroyl-glucoside) | db_source |
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| Predicted Properties | |
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| Chemical Formula | C31H29O13 |
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| IUPAC name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium |
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| InChI Identifier | InChI=1S/C31H28O13/c1-40-23-10-16(5-8-20(23)34)30-24(13-19-21(35)11-18(33)12-22(19)42-30)43-31-29(39)28(38)27(37)25(44-31)14-41-26(36)9-4-15-2-6-17(32)7-3-15/h2-13,25,27-29,31,37-39H,14H2,1H3,(H3-,32,33,34,35,36)/p+1/t25-,27-,28+,29-,31?/m1/s1 |
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| InChI Key | MFHMTMFSFNMTFQ-RJBRRTDCSA-O |
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| Isomeric SMILES | [H][C@]1(COC(=O)\C=C\C2=CC=C(O)C=C2)OC(OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC(OC)=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O |
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| Average Molecular Weight | 609.5542 |
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| Monoisotopic Molecular Weight | 609.160816014 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. |
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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 3-O-6-p-coumaroyl glycosides |
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| Alternative Parents | |
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| Substituents | - Anthocyanidin 3-o-6-p-coumaroyl-glycoside
- Anthocyanidin-3-o-glycoside
- Anthocyanin
- Flavonoid-3-o-glycoside
- 3p-methoxyflavonoid-skeleton
- Hydroxyflavonoid
- 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- Anthocyanidin
- Coumaric acid ester
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid or derivatives
- Cinnamic acid ester
- O-glycosyl compound
- Glycosyl compound
- Methoxyphenol
- 1-benzopyran
- Benzopyran
- Phenoxy compound
- Methoxybenzene
- Anisole
- Styrene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Fatty acid ester
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Oxane
- Monosaccharide
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Heteroaromatic compound
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Acetal
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- 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 | Not Available | |
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| Melting Point | Not Available | |
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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 | Not Available | |
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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-0000009000-43946c30ccb21f8c3a49 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0000019000-a3ca0a3c237d15086ee2 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-0932033000-0d86a168d0f28aed3c0b | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000009000-f61693efe4cac6807b0d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1000009000-a2cd56a698ca2b0765bf | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-8920010000-cfb4679e6a2b9bead127 | 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 | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 52 |
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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 | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | PAEONIDIN-3-(6-P-COUMAROYLGLUCOSIDE) |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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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 | Not Available |
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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 | Not Available |
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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 | — 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).
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