Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:04:34 UTC |
---|
Update date | 2020-09-17 15:41:41 UTC |
---|
Primary ID | FDB000455 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Theobromine |
---|
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. |
---|
CAS Number | 83-67-0 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione | ChEBI | 3,7-Dimethylpurine-2,6-dione | ChEBI | 3,7-Dimethylxanthine | ChEBI | Theobromin | ChEBI | Teobromin | HMDB | 2,6-Dihydroxy-3,7-dimethyl-purine | HMDB | 3,7-Dimethyl-xanthine | HMDB | Diurobromine | HMDB | 1H-Purine-2,6-dione, 3, 7-dihydro-3,7-dimethyl- | biospider | 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl- | biospider | 1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI) | biospider | 2,6-Dihydroxy-3,7-dimethylpurine | biospider | 3-7-DIMETHYLXANTHINE | biospider | 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 9CI | db_source | 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione | biospider | 3,7-dimethylpurine-2,6-dione | biospider | FEMA 3591 | db_source | Santheose | db_source | Theobromine [ban] | biospider | Theobrominum | biospider | Theosalvose | biospider | Theostene | biospider | Thesal | db_source | Thesodate | biospider | Xanthine, 3,7-dimethyl- | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C7H8N4O2 |
---|
IUPAC name | 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
---|
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) |
---|
InChI Key | YAPQBXQYLJRXSA-UHFFFAOYSA-N |
---|
Isomeric SMILES | CN1C=NC2=C1C(=O)NC(=O)N2C |
---|
Average Molecular Weight | 180.164 |
---|
Monoisotopic Molecular Weight | 180.06472552 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Imidazopyrimidines |
---|
Sub Class | Purines and purine derivatives |
---|
Direct Parent | Xanthines |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: Biological role: |
---|
Foods | Cocoa and cocoa products Beverages: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 46.67%; H 4.48%; N 31.10%; O 17.76% | DFC |
---|
Melting Point | Mp 351° | DFC |
---|
Boiling Point | Subl. 290° | DFC |
---|
Experimental Water Solubility | 0.33 mg/mL at 25 oC | YALKOWSKY,SH & HE,Y (2003) |
---|
Experimental logP | -0.78 | HANSCH,C ET AL. (1995) |
---|
Experimental pKa | pKa2 10 (25°) | DFC |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
NMR | Type | Description | | View |
---|
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 |
|
---|
External Links |
---|
ChemSpider ID | 5236 |
---|
ChEMBL ID | CHEMBL1114 |
---|
KEGG Compound ID | C07480 |
---|
Pubchem Compound ID | 5429 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 28946 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB01412 |
---|
HMDB ID | HMDB02825 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | BCL39-R:BCL39-R |
---|
EAFUS ID | 3651 |
---|
Dr. Duke ID | THEOBROMINE |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00001509 |
---|
HET ID | 37T |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Theobromine |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
anorexic | 50780 | An agent which regulates the physiologic mechanisms that control the appetite and food intake. | DUKE | anti asthmatic | 49167 | A drug used to treat asthma. | DUKE | anti cellulitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | arteriodilator | | | DUKE | bronchodilator | 35523 | An agent that causes an increase in the expansion of a bronchus or bronchial tubes. | DUKE | cAMP inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | cAMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | cGMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | central nervous system stimulant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | DUKE | emetic | | | DUKE | fetotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | myocardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | myorelaxant | | | DUKE | myostimulant | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | stimulant | | | DUKE | teratogenic | 50905 | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. | DUKE | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE |
|
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Adenosine receptor A1 | ADORA1 | P30542 | Adenosine receptor A2a | ADORA2A | P29274 |
|
---|
Pathways | |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
|
|
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
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.
|
---|