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

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

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)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
CaffeineN-containing compoundsAlkaloidsPurine and pyrimidine alkaloidsShow Food Phytochemical
Cocoa purinesN-containing compoundsAlkaloidsPurine and pyrimidine alkaloidsShow Food Phytochemical
TheobromineN-containing compoundsAlkaloidsPurine and pyrimidine alkaloidsShow Food Phytochemical
TheophyllineN-containing compoundsAlkaloidsPurine and pyrimidine alkaloidsShow 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 IDSourceDescriptionView
PFs000002PeakForestCaffeine; LC-ESI-QTOF Bruker; MS; POSITIVE; View Spectra
PFs000003PeakForestCaffeine; LC-ESI-Orbitrap; MS; POSITIVE; View Spectra
PFs000004PeakForestCaffeine; LC-ESI-Orbitrap; MS; POSITIVE; View Spectra
PFs000005PeakForestCaffeine; LC-ESI-Orbitrap; MS2; POSITIVE; CE 40 eV; View Spectra

Spectra from Online Resources

Record IDSourceDescriptionView
BML00696MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00705MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00714MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML80860MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
EA030301MassBankLC-ESI-ITFT Spectrum - 35 % (nominal), unspecifiedView Spectra
EA030302MassBankLC-ESI-ITFT Spectrum - 15 % (nominal), unspecifiedView Spectra
EA030303MassBankLC-ESI-ITFT Spectrum - 30 % (nominal), unspecifiedView Spectra
EA030304MassBankLC-ESI-ITFT Spectrum - 45 % (nominal), unspecifiedView Spectra
EA030305MassBankLC-ESI-ITFT Spectrum - 60 % (nominal), unspecifiedView Spectra
EA030306MassBankLC-ESI-ITFT Spectrum - 75 % (nominal), unspecifiedView Spectra
EA030307MassBankLC-ESI-ITFT Spectrum - 90 % (nominal), unspecifiedView Spectra
EA030308MassBankLC-ESI-ITFT Spectrum - 15 % (nominal), unspecifiedView Spectra
EA030309MassBankLC-ESI-ITFT Spectrum - 30 % (nominal), unspecifiedView Spectra
EA030310MassBankLC-ESI-ITFT Spectrum - 45 % (nominal), unspecifiedView Spectra
EA030311MassBankLC-ESI-ITFT Spectrum - 60 % (nominal), unspecifiedView Spectra
EA030312MassBankLC-ESI-ITFT Spectrum - 75 % (nominal), unspecifiedView Spectra
EA030313MassBankLC-ESI-ITFT Spectrum - 90 % (nominal), unspecifiedView Spectra
EA030314MassBankLC-ESI-ITFT Spectrum - 35 % (nominal), unspecifiedView Spectra
FIO00568MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00569MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00570MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00571MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00572MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
JP000558MassBankEI-B Spectrum - -, [M]+*View Spectra
JP003477MassBankEI-B Spectrum - -, [M]+*View Spectra
JP003511MassBankEI-B Spectrum - -, [M]+*View Spectra
KO002537MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO002538MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO002539MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO002540MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO002541MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KZ000017MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
KZ000113MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
MT000087MassBankLC-ESI-IT Spectrum - 40, unspecifiedView Spectra
OUF00133MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB003781MassBankLC-ESI-QQ Spectrum - 25 eV, unspecifiedView Spectra
PB003782MassBankLC-ESI-QQ Spectrum - 30 eV, unspecifiedView Spectra
PB003783MassBankLC-ESI-QQ Spectrum - 35 eV, unspecifiedView Spectra
PM016402ReSpectN/A Spectrum - 20%, [M+H]+View Spectra
PM018509ReSpectN/A Spectrum - 15eV, [M+H]+View Spectra
PM018510ReSpectN/A Spectrum - 30eV, [M+H]+View Spectra
PM018511ReSpectN/A Spectrum - 15eV, [M+H]+View Spectra
PM018512ReSpectN/A Spectrum - 30eV, [M+H]+View Spectra
PR010011MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR100025MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100026MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra
PS004501ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS004502ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS004503ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS004504ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS004505ReSpectN/A Spectrum - 50, [M+H]+View Spectra
PS004506ReSpectN/A Spectrum - 60, [M+H]+View Spectra
UF408901MassBankLC-ESI-ITFT Spectrum - 35, unspecifiedView Spectra
UF408902MassBankLC-ESI-ITFT Spectrum - 55, unspecifiedView Spectra
UF408903MassBankLC-ESI-ITFT Spectrum - 50, unspecifiedView Spectra
UF408904MassBankLC-ESI-ITFT Spectrum - 80, unspecifiedView Spectra
WA000948MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA000949MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA000950MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA000951MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra
WA000952MassBankLC-ESI-Q Spectrum - -, unspecifiedView Spectra

Food Sources

NameGroup
Arabica coffeeCoffee and coffee products PublicationsShow
Black teaTeas and herbal teas PublicationsShow
BlackcurrantFruit, Berries PublicationsShow
ChocolateCocoa and cocoa products PublicationsShow
CocoaCocoa and cocoa products PublicationsShow
Cocoa beanCocoa and cocoa products PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
Green teaTeas and herbal teas PublicationsShow
Green/roasted coffeeCoffee and coffee products PublicationsShow
GuaranaBeverages, Non-alcoholic PublicationsShow
MateTeas and herbal teas PublicationsShow
Mocha coffeeCoffee and coffee products PublicationsShow
Roasted coffeeCoffee and coffee products PublicationsShow
SodaBeverages, Non-alcoholic PublicationsShow
TeaTeas and herbal teas PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
CaffeineArabica coffeeCoffee and coffee products PublicationsShow
TheobromineArabica coffeeCoffee and coffee products PublicationsShow
CaffeineBlack teaTeas and herbal teas PublicationsShow
CaffeineBlackcurrantFruit, Berries PublicationsShow
CaffeineChocolateCocoa and cocoa products PublicationsShow
TheobromineChocolateCocoa and cocoa products PublicationsShow
CaffeineCocoaCocoa and cocoa products PublicationsShow
Cocoa purinesCocoaCocoa and cocoa products PublicationsShow
TheobromineCocoaCocoa and cocoa products PublicationsShow
CaffeineCocoa beanCocoa and cocoa products PublicationsShow
TheobromineCocoa beanCocoa and cocoa products PublicationsShow
TheophyllineCocoa beanCocoa and cocoa products PublicationsShow
CaffeineCoffeeCoffee and coffee products PublicationsShow
CaffeineGreen teaTeas and herbal teas PublicationsShow
CaffeineGreen/roasted coffeeCoffee and coffee products PublicationsShow
TheobromineGreen/roasted coffeeCoffee and coffee products PublicationsShow
CaffeineGuaranaBeverages, Non-alcoholic PublicationsShow
TheobromineGuaranaBeverages, Non-alcoholic PublicationsShow
TheophyllineGuaranaBeverages, Non-alcoholic PublicationsShow
CaffeineMateTeas and herbal teas PublicationsShow
TheobromineMateTeas and herbal teas PublicationsShow
TheophyllineMateTeas and herbal teas PublicationsShow
CaffeineMocha coffeeCoffee and coffee products PublicationsShow
CaffeineRoasted coffeeCoffee and coffee products PublicationsShow
TheobromineRoasted coffeeCoffee and coffee products PublicationsShow
TheophyllineRoasted coffeeCoffee and coffee products PublicationsShow
CaffeineSodaBeverages, Non-alcoholic PublicationsShow
CaffeineTeaTeas and herbal teas PublicationsShow
TheobromineTeaTeas and herbal teas PublicationsShow
TheophyllineTeaTeas and herbal teas PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeine Caffeinehumanplasma, serum, urineunchanged1h-3h>20µmol/L1-5%C8H10N4O2194.080375578 Detailed Intervention Studies Publications
Caffeine Theobrominehumanplasma, urinehost metabolism1h-3h5-20µmol/L1-5%C7H8N4O2180.064725514 Detailed Intervention Studies Publications
Caffeine Theophyllinehumanplasma, serum, urinehost metabolism1h-3h2-5µmol/L1-5%C7H8N4O2180.064725514 Detailed Intervention Studies Publications
Caffeine 1,3-dimethyluric acidhumanplasma, urinehost metabolism5h-8h50-200 nmol/L1-5%C7H8N4O3196.059640134 Detailed Intervention Studies Publications
Caffeine 1,3,7-Trimethyluric acidhumanblood, urinehost metabolismNot AvailableNot Available1-5%C8H10N4O3210.075290198 Detailed Intervention Studies Publications
Caffeine 1-methylxanthinehumanblood, urinehost metabolismNot AvailableNot Available10-30%C6H6N4O2166.049075449 Detailed Intervention Studies Publications
Caffeine 5-acetyl-amino-6-amino-3-methyluracilhumanurinehost metabolismNot AvailableNot Available10-30%C7H10N4O3198.075290198 Detailed Intervention Studies Publications
Caffeine 5-acetylamino-6-formylamino-3-methyluracilhumanurinehost metabolismNot AvailableNot Available5-10%C8H10N4O4226.070204818 Detailed Intervention Studies Publications
Caffeine Paraxanthinehumanplasma, urinehost metabolism5h-8h2-5µmol/L1-5%C7H8N4O2180.064725514 Detailed Intervention Studies Publications
Caffeine 1-methyluric acidhumanurinehost metabolismNot AvailableNot Available10-30%C6H6N4O3182.043990069 Detailed Intervention Studies Publications
Caffeine 1,7-dimethyluricacidhumanplasma, urinehost metabolismNot AvailableNot Available5-10%C7H8N4O3196.059640134 Detailed Intervention Studies Publications
Caffeine 3-methylxanthinehumanurinehost metabolismNot AvailableNot Available1-5%C6H6N4O2166.049075449 Detailed Intervention Studies Publications
Caffeine 7-methylxanthinehumanurinehost metabolismNot AvailableNot Available1-5%C6H6N4O2166.049075449 Detailed Intervention Studies Publications
Caffeine 7-methyluric acidhumanurinehost metabolismNot AvailableNot Available5-10%C6H6N4O3182.043990069 Detailed Intervention Studies
Caffeine 3-Methyluric acidhumanurinehost metabolismNot AvailableNot Available1-5%C6H6N4O3182.043990069 Detailed Intervention Studies Publications
Caffeine 6-Amino-5(N-methylformylamino)-1-methyluracilNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC7H10N4O3198.075290198 Detailed Intervention Studies
Caffeine 4-Amino-(5-formylmethyl- amino) 1,3-dimethyluracilhumanNot Availablehost metabolismNot AvailableNot Available1-5%C7H10N4O3198.075290198 Detailed Intervention Studies
Cocoa purines CaffeineNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H10N4O2194.080375578 Detailed Intervention Studies
Theobromine Caffeinehumanplasmahost metabolism<1h5-20µmol/LNot AvailableC8H10N4O2194.080375578 Detailed Intervention Studies Publications
Theophylline CaffeineNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H10N4O2194.080375578 Detailed Intervention Studies
Back