Caffeine
precursor
Showing entry for Caffeine
Identification
- PhytoHub ID
- PHUB000789
- Name
- Caffeine
- Systematic Name
- 1,3,7-trimethylxanthine
- Synonyms
- 1,3,7-trimethylxanthine
- 3-Methyltheobromine
- Coffeine
- Guaranine
- Thein
- Theine
- CAS Number
- 58-08-2
- Average Mass
- 194.194
- Monoisotopic Mass
- 194.080375578
- Chemical Formula
- C8H10N4O2
- IUPAC Name
- 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
- InChI Key
- RYYVLZVUVIJVGH-UHFFFAOYSA-N
- InChI Identifier
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
- SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C
- Structure
Structure for Caffeine
Calculated Properties
- Solubility (ALOGPS)
- 1.10e+01 g/l
- LogS (ALOGPS)
- -1.25
- LogP (ALOGPS)
- -0.24
- Hydrogen Acceptors
- 3
- Hydrogen Donors
- 0
- Rotatable Bond Count
- 0
- Polar Surface Area
- 58.440000000000005
- Refractivity
- 49.8312
- Polarizability
- 18.9549309213843
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -1.1587287861082745
- pKa (strongest acidic)
- Not Available
- Number of Rings
- 2
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- PubChem
- 2519
- ChEBI
- 27732
- FooDB (Foods)
- FDB002100
- Chemistry Dashboard
- DTXSID0020232
- KNApSAcK
- C00001492
- MetaboLights
- MTBLC27732
- Exposome Explorer
- 567
- PeakForestCompound
- 000614
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", "purine alkaloid", "trimethylxanthine"]
- 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"]
PeakForest Spectra ( Experimental Spectra from Phytohub Collaborators )
| Record ID | Source | Description | View |
|---|---|---|---|
| PFs000002 | PeakForest | Caffeine; LC-ESI-QTOF Bruker; MS; POSITIVE; | View Spectra |
| PFs000003 | PeakForest | Caffeine; LC-ESI-Orbitrap; MS; POSITIVE; | View Spectra |
| PFs000004 | PeakForest | Caffeine; LC-ESI-Orbitrap; MS; POSITIVE; | View Spectra |
| PFs000005 | PeakForest | Caffeine; LC-ESI-Orbitrap; MS2; POSITIVE; CE 40 eV; | View Spectra |
Spectra from Phytohub
| Spectrum Type | Instrument Type | Technology | Ion Mode | Collision Energy | View | |
|---|---|---|---|---|---|---|
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-MS | Not Available | Not Available | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=HITACHI M-80 | positive | Not Available | View Spectrum | |
| GC-MS | CI-B | instrument=Unknown | positive | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=HITACHI M-60 | positive | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=HITACHI M-68 | positive | Not Available | View Spectrum | |
| GC-MS | CI-B | instrument=HITACHI M-60 | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-MS | Not Available | Not Available | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Ei | Not Available | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 10V | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 25V | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 40V | View Spectrum | |
| LC-MS/MS | EI-B (HITACHI M-80) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | CI-B (Unknown) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | EI-B (HITACHI M-60) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | EI-B (HITACHI M-68) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | CI-B (HITACHI M-60) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Positive | 10V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Positive | 20V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Positive | 30V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Positive | 40V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Positive | 50V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Positive | 30V | View Spectrum | |
| LC-MS/MS | DI-ESI-qTof | From GNPS Library | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-qTof | From GNPS Library | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-ITFT | instrument=LTQ Orbitrap XL Thermo Scientific | positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-ITFT | instrument=LTQ Orbitrap XL Thermo Scientific | positive | V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 40V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 40V | View Spectrum |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Arabica coffee | Coffee and coffee products | Publications | Show | |
| Black tea | Teas and herbal teas | Publications | Show | |
| Blackcurrant | Fruit, Berries | Publications | Show | |
| Chocolate | Cocoa and cocoa products | Publications | Show | |
| Cocoa | Cocoa and cocoa products | Publications | Show | |
| Cocoa bean | Cocoa and cocoa products | Publications | Show | |
| Coffee | Coffee and coffee products | Publications | Show | |
| Green tea | Teas and herbal teas | Publications | Show | |
| Green/roasted coffee | Coffee and coffee products | Publications | Show | |
| Guarana | Beverages, Non-alcoholic | Publications | Show | |
| Mate | Teas and herbal teas | Publications | Show | |
| Mocha coffee | Coffee and coffee products | Publications | Show | |
| Roasted coffee | Coffee and coffee products | Publications | Show | |
| Soda | Beverages, Non-alcoholic | 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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caffeine | Caffeine | human | plasma, serum, urine | unchanged | 1h-3h | >20µmol/L | 1-5% | C8H10N4O2 | 194.080375578 | 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 | ||
| Caffeine | Theophylline | human | plasma, serum, urine | host metabolism | 1h-3h | 2-5µmol/L | 1-5% | C7H8N4O2 | 180.064725514 | Detailed Intervention Studies | Publications | ||
| Caffeine | 1,3-dimethyluric acid | human | plasma, urine | host metabolism | 5h-8h | 50-200 nmol/L | 1-5% | C7H8N4O3 | 196.059640134 | Detailed Intervention Studies | Publications | ||
| Caffeine | 1,3,7-Trimethyluric acid | human | blood, urine | host metabolism | Not Available | Not Available | 1-5% | C8H10N4O3 | 210.075290198 | Detailed Intervention Studies | Publications | ||
| Caffeine | 1-methylxanthine | human | blood, urine | host metabolism | Not Available | Not Available | 10-30% | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications | ||
| Caffeine | 5-acetyl-amino-6-amino-3-methyluracil | human | urine | host metabolism | Not Available | Not Available | 10-30% | C7H10N4O3 | 198.075290198 | Detailed Intervention Studies | Publications | ||
| Caffeine | 5-acetylamino-6-formylamino-3-methyluracil | human | urine | host metabolism | Not Available | Not Available | 5-10% | C8H10N4O4 | 226.070204818 | Detailed Intervention Studies | Publications | ||
| Caffeine | Paraxanthine | human | plasma, urine | host metabolism | 5h-8h | 2-5µmol/L | 1-5% | C7H8N4O2 | 180.064725514 | Detailed Intervention Studies | Publications | ||
| Caffeine | 1-methyluric acid | human | urine | host metabolism | Not Available | Not Available | 10-30% | C6H6N4O3 | 182.043990069 | Detailed Intervention Studies | Publications | ||
| Caffeine | 1,7-dimethyluricacid | human | urine | host metabolism | Not Available | Not Available | 5-10% | C7H8N4O3 | 196.059640134 | Detailed Intervention Studies | Publications | ||
| Caffeine | 3-methylxanthine | human | urine | host metabolism | Not Available | Not Available | 1-5% | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications | ||
| Caffeine | 7-methylxanthine | human | urine | host metabolism | Not Available | Not Available | 1-5% | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications | ||
| Caffeine | 7-methyluric acid | human | urine | host metabolism | Not Available | Not Available | 5-10% | C6H6N4O3 | 182.043990069 | Detailed Intervention Studies | Publications | ||
| Caffeine | 3-Methyluric acid | human | urine | host metabolism | Not Available | Not Available | 1-5% | C6H6N4O3 | 182.043990069 | Detailed Intervention Studies | Publications | ||
| Caffeine | 4-Amino-(5-formylmethyl- amino) 1,3-dimethyluracil | human | urine | host metabolism | Not Available | Not Available | 1-5% | C7H10N4O3 | 198.075290198 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value | |||
|---|---|---|---|---|---|---|
| Caffeine | Caffeine | Smoking | No effect | Publications | ||
| Caffeine | Theophylline | Age | No effect | Publications | ||
| Caffeine | 1,3-dimethyluric acid | Age | No effect | Publications | ||
| Caffeine | 1,3-dimethyluric acid | Smoking | No effect | Publications | ||
| Caffeine | 1,3,7-Trimethyluric acid | Smoking | No effect | Publications | ||
| Caffeine | 5-acetyl-amino-6-amino-3-methyluracil | Bmi | Effect, clusters | Publications | ||
| Caffeine | Paraxanthine | Age | No effect | Publications | ||
| Caffeine | 3-methylxanthine | Age | No effect | Publications | ||
| Caffeine | 3-methylxanthine | Smoking | No effect | Publications | ||
| Caffeine | 7-methylxanthine | Age | No effect | Publications | ||
| Caffeine | 3-Methyluric acid | Age | Effect, clusters | Publications | ||
| Caffeine | 3-Methyluric acid | Smoking | No effect | Publications |