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 23:40:30 UTC |
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Update Date | 2022-03-07 02:55:44 UTC |
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HMDB ID | HMDB0038370 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common 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 peach (var.), pears (Pyrus communis), and kiwis (Actinidia chinensis). Procyanidin C1 has also been detected, but not quantified in, several different foods, such as apple cider, green zucchinis (Cucurbita pepo var. cylindrica), cucurbita (Cucurbita), common wheats (Triticum aestivum), and common peas (Pisum sativum). This could make procyanidin C1 a potential biomarker for the consumption of these foods. Procyanidin C1 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Procyanidin C1. |
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Structure | [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 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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Synonyms | Value | 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 |
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Chemical Formula | C45H38O18 |
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Average Molecular Weight | 866.781 |
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Monoisotopic Molecular Weight | 866.205814384 |
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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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Traditional Name | proanthocyanidin C1 |
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CAS Registry Number | 37064-30-5 |
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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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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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Chemical Taxonomy |
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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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Not Available | Not Available |
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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 | 140.0 - 142.0 °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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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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 - Procyanidin C1 LC-ESI-QTOF , negative-QTOF | splash10-016r-0340210090-7a35b5c8f1ccbf9ce4fe | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 10V, Positive-QTOF | splash10-014j-0100005690-161c67165e6b61ef57bb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 20V, Positive-QTOF | splash10-0005-0100095720-02cbe7a0c9e7f5b22731 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 40V, Positive-QTOF | splash10-005a-0000091310-a37ac8e1536b30e63a1e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 10V, Negative-QTOF | splash10-014i-0000000290-d007b6b11a94570a4ea1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 20V, Negative-QTOF | splash10-0f79-0940310530-208f53a241f13af95f6b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 40V, Negative-QTOF | splash10-002r-0970202200-0b6a6c3437423c0f510f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 10V, Negative-QTOF | splash10-014i-0000000090-1908e9268dd08c7b8ec0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 20V, Negative-QTOF | splash10-0ap0-0000000590-e0e939b2b90e92e9b2ee | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 40V, Negative-QTOF | splash10-05n1-0250010790-9209726cb0057ab3be6f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 10V, Positive-QTOF | splash10-066r-0000000690-607bdbb728e2f09d08f3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 20V, Positive-QTOF | splash10-014i-0100020590-0d606c193a998f7c0b1c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Procyanidin C1 40V, Positive-QTOF | splash10-0109-0910000580-1c47f69a0c96e4c8ee37 | 2021-09-23 | Wishart Lab | View Spectrum |
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