Theobromine
precursor
Showing entry for Theobromine
Identification
- PhytoHub ID
- PHUB000790
- Name
- Theobromine
- Systematic Name
- 3,7-Dimethylxanthine
- Synonyms
- 3,7-Dimethylxanthine
- Thesal
- CAS Number
- 83-67-0
- Average Mass
- 180.167
- Monoisotopic Mass
- 180.064725514
- Chemical Formula
- C7H8N4O2
- IUPAC Name
- 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
- InChI Key
- YAPQBXQYLJRXSA-UHFFFAOYSA-N
- 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)
- SMILES
CN1C=NC2=C1C(=O)NC(=O)N2C
- Structure
Structure for Theobromine
Calculated Properties
- Solubility (ALOGPS)
- 9.74e+00 g/l
- LogS (ALOGPS)
- -1.27
- LogP (ALOGPS)
- -0.46
- Hydrogen Acceptors
- 3
- Hydrogen Donors
- 1
- Rotatable Bond Count
- 0
- Polar Surface Area
- 67.23
- Refractivity
- 44.9345
- Polarizability
- 16.85017806003434
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -1.1414249896669322
- pKa (strongest acidic)
- 9.243345307813192
- Number of Rings
- 2
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- PubChem
- 5429
- ChEBI
- 28946
- Chemistry Dashboard
- DTXSID9026132
- KNApSAcK
- C00001509
- MetaboLights
- MTBLC28946
- FooDB (Compounds)
- FDB000455
- PeakForestCompound
- 000615
Taxonomy as Food Phytochemical
- Family
- N-containing compounds
- Class
- Alkaloids
- Sub-class
- Purines and pyrimidines
Taxonomy as Metabolite
- Metabolite Family
- N-containing compound metabolites
- Metabolite Class
- Alkaloid metabolites
- Metabolite Sub-class
- Purines and pyrimidines (parent, host and microbial metabolites)
Taxonomy of its Food Phytochemical Precursor(s)
| Food Phytochemical | Family | Class | Sub-class | |
|---|---|---|---|---|
| Caffeine | N-containing compounds | Alkaloids | Purines and pyrimidines | Show Food Phytochemical |
| Theobromine | N-containing compounds | Alkaloids | Purines and pyrimidines | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Imidazopyrimidines
- Super-class
- Organoheterocyclic compounds
- Sub-class
- Purines and purine derivatives
- Direct Parent Name
- Xanthines
- Alternative Parent Names
- ["6-oxopurines", "Alkaloids and derivatives", "Azacyclic compounds", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Lactams", "N-substituted imidazoles", "Organic oxides", "Organonitrogen compounds", "Organooxygen compounds", "Organopnictogen compounds", "Pyrimidones", "Ureas", "Vinylogous amides"]
- External Descriptor Annotations
- ["Purine alkaloids", "a small molecule", "dimethylxanthine"]
- Substituent Names
- ["6-oxopurine", "Alkaloid or derivatives", "Aromatic heteropolycyclic compound", "Azacycle", "Azole", "Heteroaromatic compound", "Hydrocarbon derivative", "Imidazole", "Lactam", "N-substituted imidazole", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Purinone", "Pyrimidine", "Pyrimidone", "Urea", "Vinylogous amide", "Xanthine"]
Spectra from Online Resources
| Record ID | Source | Description | View |
|---|---|---|---|
| BML01074 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
| BML01082 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
| BML82245 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
| CO000476 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
| CO000477 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
| CO000478 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
| CO000479 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
| CO000480 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
| JP002808 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
| KO004122 | MassBank | LC-ESI-QQ Spectrum - 10 V, unspecified | View Spectra |
| KO004123 | MassBank | LC-ESI-QQ Spectrum - 20 V, unspecified | View Spectra |
| KO004124 | MassBank | LC-ESI-QQ Spectrum - 30 V, unspecified | View Spectra |
| KO004125 | MassBank | LC-ESI-QQ Spectrum - 40 V, unspecified | View Spectra |
| KO004126 | MassBank | LC-ESI-QQ Spectrum - 50 V, unspecified | View Spectra |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Arabica coffee | Coffee and coffee products | Publications | Show | |
| Chocolate | Cocoa and cocoa products | Publications | Show | |
| Cocoa | Cocoa and cocoa products | Publications | Show | |
| Cocoa bean | Cocoa and cocoa products | Publications | Show | |
| Green/roasted coffee | Coffee and coffee products | Publications | Show | |
| Guarana | Beverages, Non-alcoholic | Publications | Show | |
| Mate | Teas and herbal teas | Publications | Show | |
| Roasted coffee | Coffee and coffee products | Publications | Show | |
| Tea | Teas and herbal teas | Publications | Show |
Food Sources of its Food Phytochemical(s)
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
| Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Theobromine | Theobromine | human | plasma | unchanged | 1h-3h | >20µmol/L | 10-30% | C7H8N4O2 | 180.064725514 | Detailed Intervention Studies | Publications | ||
| Theobromine | 1-methylxanthine | human | plasma | host metabolism | <1h | 0.5-2µmol/L | Not Available | C6H6N4O2 | 166.049075449 | Publications | |||
| Theobromine | 3,7 dimethyluric acid | human | urine | host metabolism | Not Available | Not Available | 1-5% | C7H8N4O3 | 196.059640134 | Detailed Intervention Studies | Publications | ||
| Theobromine | 1,7-dimethyluricacid | human | plasma | host metabolism | 5h-8h | 50-200 nmol/L | Not Available | C7H8N4O3 | 196.059640134 | Publications | |||
| Theobromine | 3-methylxanthine | human | urine | host metabolism | Not Available | Not Available | 10-30% | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications | ||
| Theobromine | 7-methylxanthine | human | urine | host metabolism | Not Available | Not Available | 30-50% | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications | ||
| Theobromine | 7-methyluric acid | human | urine | host metabolism | Not Available | Not Available | 5-10% | C6H6N4O3 | 182.043990069 | Detailed Intervention Studies | Publications | ||
| Theobromine | 6-Amino-5(N-methylformylamino)-1-methyluracil | human | urine | host metabolism | Not Available | Not Available | 5-10% | C7H10N4O3 | 198.075290198 | Detailed Intervention Studies | Publications | ||
| Caffeine | Theobromine | human | plasma, urine | host metabolism | 1h-3h | 5-20µmol/L | 1-5% | C7H8N4O2 | 180.064725514 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value | |||
|---|---|---|---|---|---|---|
| Theobromine | 1-methylxanthine | Age | No effect | Publications | ||
| Theobromine | 3,7 dimethyluric acid | Age | Effect, clusters | Publications | ||
| Theobromine | 3-methylxanthine | Smoking | No effect | Publications | ||
| Theobromine | 3-methylxanthine | Age | No effect | Publications | ||
| Theobromine | 7-methylxanthine | |||||
| Theobromine | 6-Amino-5(N-methylformylamino)-1-methyluracil | Smoking | Effect, clusters | Publications |