Caffeine
precursor
Showing entry for Caffeine
Identification
- PhytoHub ID
- PHUB000789
- Name
- Caffeine
- Systematic Name
- Not Available
- 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
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
- Purine and pyrimidine alkaloids
Taxonomy as Metabolite
- Metabolite Family
- N-containing compound metabolites
- Metabolite Class
- Alkaloid metabolites
- Metabolite Sub-class
- Purines and pyrimidines (parent, host and microbial metabolites)
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 Online Resources
Record ID | Source | Description | View |
---|---|---|---|
BML00696 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00705 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML00714 | MassBank | LC-ESI-QTOF Spectrum - 40 ev, unspecified | View Spectra |
BML80860 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
EA030301 | MassBank | LC-ESI-ITFT Spectrum - 35 % (nominal), unspecified | View Spectra |
EA030302 | MassBank | LC-ESI-ITFT Spectrum - 15 % (nominal), unspecified | View Spectra |
EA030303 | MassBank | LC-ESI-ITFT Spectrum - 30 % (nominal), unspecified | View Spectra |
EA030304 | MassBank | LC-ESI-ITFT Spectrum - 45 % (nominal), unspecified | View Spectra |
EA030305 | MassBank | LC-ESI-ITFT Spectrum - 60 % (nominal), unspecified | View Spectra |
EA030306 | MassBank | LC-ESI-ITFT Spectrum - 75 % (nominal), unspecified | View Spectra |
EA030307 | MassBank | LC-ESI-ITFT Spectrum - 90 % (nominal), unspecified | View Spectra |
EA030308 | MassBank | LC-ESI-ITFT Spectrum - 15 % (nominal), unspecified | View Spectra |
EA030309 | MassBank | LC-ESI-ITFT Spectrum - 30 % (nominal), unspecified | View Spectra |
EA030310 | MassBank | LC-ESI-ITFT Spectrum - 45 % (nominal), unspecified | View Spectra |
EA030311 | MassBank | LC-ESI-ITFT Spectrum - 60 % (nominal), unspecified | View Spectra |
EA030312 | MassBank | LC-ESI-ITFT Spectrum - 75 % (nominal), unspecified | View Spectra |
EA030313 | MassBank | LC-ESI-ITFT Spectrum - 90 % (nominal), unspecified | View Spectra |
EA030314 | MassBank | LC-ESI-ITFT Spectrum - 35 % (nominal), unspecified | View Spectra |
FIO00568 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
FIO00569 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
FIO00570 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
FIO00571 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
FIO00572 | MassBank | LC-ESI-QTOF Spectrum - 50 eV, unspecified | View Spectra |
JP000558 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
JP003477 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
JP003511 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
KO002537 | MassBank | LC-ESI-QQ Spectrum - 10 V, unspecified | View Spectra |
KO002538 | MassBank | LC-ESI-QQ Spectrum - 20 V, unspecified | View Spectra |
KO002539 | MassBank | LC-ESI-QQ Spectrum - 30 V, unspecified | View Spectra |
KO002540 | MassBank | LC-ESI-QQ Spectrum - 40 V, unspecified | View Spectra |
KO002541 | MassBank | LC-ESI-QQ Spectrum - 50 V, unspecified | View Spectra |
KZ000017 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
KZ000113 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
MT000087 | MassBank | LC-ESI-IT Spectrum - 40, unspecified | View Spectra |
OUF00133 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PB003781 | MassBank | LC-ESI-QQ Spectrum - 25 eV, unspecified | View Spectra |
PB003782 | MassBank | LC-ESI-QQ Spectrum - 30 eV, unspecified | View Spectra |
PB003783 | MassBank | LC-ESI-QQ Spectrum - 35 eV, unspecified | View Spectra |
PM016402 | ReSpect | N/A Spectrum - 20%, [M+H]+ | View Spectra |
PM018509 | ReSpect | N/A Spectrum - 15eV, [M+H]+ | View Spectra |
PM018510 | ReSpect | N/A Spectrum - 30eV, [M+H]+ | View Spectra |
PM018511 | ReSpect | N/A Spectrum - 15eV, [M+H]+ | View Spectra |
PM018512 | ReSpect | N/A Spectrum - 30eV, [M+H]+ | View Spectra |
PR010011 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PR100025 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
PR100026 | MassBank | LC-ESI-QTOF Spectrum - 30 V, unspecified | View Spectra |
PS004501 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS004502 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS004503 | ReSpect | N/A Spectrum - 30, [M+H]+ | View Spectra |
PS004504 | ReSpect | N/A Spectrum - 40, [M+H]+ | View Spectra |
PS004505 | ReSpect | N/A Spectrum - 50, [M+H]+ | View Spectra |
PS004506 | ReSpect | N/A Spectrum - 60, [M+H]+ | View Spectra |
UF408901 | MassBank | LC-ESI-ITFT Spectrum - 35, unspecified | View Spectra |
UF408902 | MassBank | LC-ESI-ITFT Spectrum - 55, unspecified | View Spectra |
UF408903 | MassBank | LC-ESI-ITFT Spectrum - 50, unspecified | View Spectra |
UF408904 | MassBank | LC-ESI-ITFT Spectrum - 80, unspecified | View Spectra |
WA000948 | MassBank | LC-ESI-Q Spectrum - -, unspecified | View Spectra |
WA000949 | MassBank | LC-ESI-Q Spectrum - -, unspecified | View Spectra |
WA000950 | MassBank | LC-ESI-Q Spectrum - -, unspecified | View Spectra |
WA000951 | MassBank | LC-ESI-Q Spectrum - -, unspecified | View Spectra |
WA000952 | MassBank | LC-ESI-Q Spectrum - -, unspecified | View Spectra |
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)
No food source information available of its precursor(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 | 1,3,7-Trimethyluric acid | human | blood, urine | host metabolism | Not Available | Not Available | Not Available | C8H10N4O3 | 210.075290198 | Detailed Intervention Studies | Publications | ||
Caffeine | 1-methylxanthine | human | blood, urine | host metabolism | Not Available | Not Available | Not Available | C6H6N4O2 | 166.049075449 | Detailed Intervention Studies | Publications |
Inter-Individual Variations Metabolism
No data on inter-individual variations available