| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:31 UTC |
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| Update date | 2019-11-26 02:54:37 UTC |
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| Primary ID | FDB000298 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Caffeoyl aspartic acid |
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| Description | Caffeoyl aspartic acid belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Caffeoyl aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeoyl aspartic acid is found, on average, in the highest concentration within cocoa powders and hot chocolates. This could make caffeoyl aspartic acid a potential biomarker for the consumption of these foods. |
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| CAS Number | 860295-20-1 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C13H13NO7 |
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| IUPAC name | 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]butanedioic acid |
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| InChI Identifier | InChI=1S/C13H13NO7/c15-9-3-1-7(5-10(9)16)2-4-11(17)14-8(13(20)21)6-12(18)19/h1-5,8,15-16H,6H2,(H,14,17)(H,18,19)(H,20,21)/b4-2+ |
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| InChI Key | YNHFZQQNJPOYRC-DUXPYHPUSA-N |
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| Isomeric SMILES | OC(=O)CC(NC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O |
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| Average Molecular Weight | 295.2448 |
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| Monoisotopic Molecular Weight | 295.069201775 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Aspartic acid and derivatives |
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| Alternative Parents | |
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| Substituents | - Aspartic acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Cinnamic acid amide
- Cinnamic acid or derivatives
- Hydroxycinnamic acid or derivatives
- Catechol
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Carbonyl group
- Organooxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organic nitrogen compound
- Organonitrogen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Biological role: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Caffeoyl aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03fr-2960000000-52338e0e7633b2e19048 | Spectrum | | Predicted GC-MS | Caffeoyl aspartic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-7219070000-4a7d3dfe7fa0eea2a3c1 | Spectrum |
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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 | splash10-003s-1590000000-f7fa4becc100b31af02c | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0079-9860000000-8b849d06f12d20207047 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-9500000000-05e18ea6b0c65b18b9c9 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6x-0290000000-21661e5932a28ee7f403 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0w5c-1690000000-2d6afb93ddddb93d1964 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03du-9700000000-78b251fb070d0d39b656 | 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 | 24891368 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 551 |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB29294 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HJB19-Y:OVP05-O |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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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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| 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 |
- Stark T, Bareuther S, Hofmann T: Molecular definition of the taste of roasted cocoa nibs (Theobroma cacao) by means of quantitative studies and sensory experiments. J Agric Food Chem. 2006 Jul 26;54(15):5530-9. Pubmed [Structure]
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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.
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