Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:13:15 UTC |
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Update date | 2019-11-26 03:15:06 UTC |
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Primary ID | FDB017710 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Procyanidin C1 |
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Description | Procyanidin C1, also known as cinnamtannin A1 or procyanidol C1, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Procyanidin C1 is found, on average, in the highest concentration within a few different foods, such as chocolate, cocoa powder, and apples (Malus pumila) and in a lower concentration in broad beans (Vicia faba), chestnuts (Castanea), and pears (Pyrus communis). Procyanidin C1 has also been detected, but not quantified in, several different foods, such as yellow zucchinis (Cucurbita pepo var. cylindrica), lettuces (Lactuca sativa), pineapples (Ananas comosus), garden tomato (var.), and fruit juice. This could make procyanidin C1 a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Procyanidin C1. |
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CAS Number | 37064-30-5 |
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Structure | |
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Synonyms | Synonym | Source |
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[Epicatechin(4b->8)]2-epicatechin | ChEBI | [Epicatechin-(4beta->8)]2-epicatechin | ChEBI | Cinnamtannin a1 | ChEBI | EC-(4b,8)-ec-(4b,8)-ec | ChEBI | Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechin | ChEBI | Proanthocyanidin C1 | ChEBI | Procyanidin trimer C1 | ChEBI | Procyanidol C1 | ChEBI | [Epicatechin-(4b->8)]2-epicatechin | Generator | [Epicatechin-(4β->8)]2-epicatechin | Generator | Epicatechin-(4b->8)-epicatechin-(4b->8)-epicatechin | Generator | Epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin | Generator | [Epicatechin(4b->8)]2epicatechin | db_source | EC-(4b,8)-EC-(4b,8)-EC | db_source | Procyanidin C1 | db_source |
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Predicted Properties | |
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Chemical Formula | C45H38O18 |
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IUPAC name | (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
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InChI Identifier | InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1 |
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InChI Key | MOJZMWJRUKIQGL-XILRTYJMSA-N |
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Isomeric SMILES | [H][C@]1([C@@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C2O[C@@H]([C@H](O)[C@@]([H])(C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC(O)=C(O)C=C3)C2=C(O)C=C1O)C1=CC(O)=C(O)C=C1 |
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Average Molecular Weight | 866.781 |
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Monoisotopic Molecular Weight | 866.205814384 |
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Classification |
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Description | Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. |
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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 | Biflavonoids and polyflavonoids |
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Direct Parent | Biflavonoids and polyflavonoids |
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Alternative Parents | |
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Substituents | - C-type proanthocyanidin
- B-type proanthocyanidin
- Bi- and polyflavonoid skeleton
- Proanthocyanidin
- Catechin
- Flavan-3-ol
- Hydroxyflavonoid
- 3'-hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 3-hydroxyflavonoid
- Flavan
- Chromane
- 1-benzopyran
- Benzopyran
- Catechol
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Ether
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- 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: Biological location: Source: |
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Role | Biological role: |
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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 62.36%; H 4.42%; O 33.23% | DFC |
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Melting Point | 140.0-142.0 oC | |
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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 +102 (H2O) | 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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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-016r-0340210090-7a35b5c8f1ccbf9ce4fe | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0100005690-161c67165e6b61ef57bb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0005-0100095720-02cbe7a0c9e7f5b22731 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-005a-0000091310-a37ac8e1536b30e63a1e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000000290-d007b6b11a94570a4ea1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f79-0940310530-208f53a241f13af95f6b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002r-0970202200-0b6a6c3437423c0f510f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000000090-1908e9268dd08c7b8ec0 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ap0-0000000590-e0e939b2b90e92e9b2ee | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05n1-0250010790-9209726cb0057ab3be6f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0000000690-607bdbb728e2f09d08f3 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0100020590-0d606c193a998f7c0b1c | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0109-0910000580-1c47f69a0c96e4c8ee37 | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 148540 |
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ChEMBL ID | CHEMBL290632 |
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KEGG Compound ID | C17624 |
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Pubchem Compound ID | 169853 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 157 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB38370 |
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CRC / DFC (Dictionary of Food Compounds) ID | KZF49-Q:KZF50-K |
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EAFUS ID | Not Available |
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Dr. Duke ID | PROANTHOCYANIDIN-C1|PROCYANIDIN-C-1 |
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BIGG ID | Not Available |
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KNApSAcK ID | C00009098 |
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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 | Proanthocyanidin_C1 |
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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 | Descriptor | ID | Definition | Reference |
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Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | CHEBI | Lipoxygenase inhibitor | 35856 | An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases. | CHEBI | Xanthine oxidase inhibitor | 35634 | An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function. | CHEBI |
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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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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