Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:34 UTC |
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Update date | 2020-09-17 15:41:41 UTC |
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Primary ID | FDB000455 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Theobromine |
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Description | Theobromine, also known as diurobromine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Theobromine is an extremely weak basic (essentially neutral) compound (based on its pKa). Theobromine is an isomer of theophylline, as well as paraxanthine. Theobromine exists in all living organisms, ranging from bacteria to humans. Within humans, theobromine participates in a number of enzymatic reactions. In particular, theobromine and formaldehyde can be biosynthesized from caffeine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In addition, theobromine can be converted into 3,7-dimethyluric acid through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, theobromine is involved in caffeine metabolism. Theobromine is a bitter tasting compound. Outside of the human body, Theobromine is found, on average, in the highest concentration within a few different foods, such as cocoa powders, chocolates, and cocoa beans and in a lower concentration in other candies, cakes, and soy milks. Theobromine has also been detected, but not quantified in, several different foods, such as hyacinth beans, oyster mushrooms, tamarinds, milk (other mammals), and watercress. This could make theobromine a potential biomarker for the consumption of these foods. Theobromine and caffeine are similar in that they are related alkaloids. A necropsy and toxicology report performed at the University of New Hampshire in 2015 confirmed they died of heart failure caused by theobromine after they consumed 41 kilograms (90 lb) of chocolate and doughnuts placed at the site as bait. |
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CAS Number | 83-67-0 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C7H8N4O2 |
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IUPAC name | 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
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InChI Identifier | InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13) |
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InChI Key | YAPQBXQYLJRXSA-UHFFFAOYSA-N |
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Isomeric SMILES | CN1C=NC2=C1C(=O)NC(=O)N2C |
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Average Molecular Weight | 180.164 |
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Monoisotopic Molecular Weight | 180.06472552 |
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Classification |
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Description | Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | Xanthines |
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Alternative Parents | |
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Substituents | - Xanthine
- 6-oxopurine
- Purinone
- Alkaloid or derivatives
- Pyrimidone
- N-substituted imidazole
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Lactam
- Urea
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Foods | Cocoa and cocoa products Beverages: |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-9700000000-770b2dc556ada7d97cae | 2015-03-01 | View Spectrum | GC-MS | Theobromine, 1 TMS, GC-MS Spectrum | splash10-0079-7980000000-efb14ee11aad17b6b4d2 | Spectrum | GC-MS | Theobromine, non-derivatized, GC-MS Spectrum | splash10-001i-6900000000-7d44855bbf11e559d96e | Spectrum | GC-MS | Theobromine, non-derivatized, GC-MS Spectrum | splash10-0079-7980000000-efb14ee11aad17b6b4d2 | Spectrum | Predicted GC-MS | Theobromine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zgr-0900000000-87a73eda89d8ce593ee8 | Spectrum | Predicted GC-MS | Theobromine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0900000000-8d639c53ad9b2b8f508e | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9300000000-0d20b5fe9b93b113a29e | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-9000000000-55968ca3e94ce5a05cfe | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-001i-6900000000-7d44855bbf11e559d96e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-001i-1900000000-1932568f11357ae32f55 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-001i-2900000000-3918185c5a4afb18f11a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0910-5900000000-b590772083f824ea0fc6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-014i-9400000000-c06ac99fd6e0c84d9653 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9100000000-3802e577174b5a4acced | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-02a9-2900000400-2ae0058f4f5f9fc23c01 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-004j-7900000000-54365e34320abc3c8f2e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-1900000000-599d34de0bc963388dc0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-2900000000-8a0fd0cd87c35684d19f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0910-5900000000-b590772083f824ea0fc6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-014i-9400000000-c06ac99fd6e0c84d9653 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-014i-9100000000-3802e577174b5a4acced | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-b1202b5f491f2aaaf542 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01qi-0900000000-d58a783853c528b7d126 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01b9-8900000000-d9e4a4411ab0ed3620a0 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-3f82b9da0450b7ae12ae | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-235bf01d7d7435b9fe54 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kai-9200000000-cb89e2e8ee405aba807d | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-fa072bef954a047da7f7 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004r-0900000000-22f6a3f6049c3a993878 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9300000000-afa55dfa675c3caec4f0 | 2017-06-28 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 5236 |
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ChEMBL ID | CHEMBL1114 |
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KEGG Compound ID | C07480 |
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Pubchem Compound ID | 5429 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28946 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01412 |
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HMDB ID | HMDB02825 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCL39-R:BCL39-R |
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EAFUS ID | 3651 |
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Dr. Duke ID | THEOBROMINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001509 |
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HET ID | 37T |
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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 | Theobromine |
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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 | |
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Enzymes | |
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Pathways | |
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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 | |
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Files |
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MSDS | show |
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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 | — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — 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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