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
caffeine
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 Precursor

Family
N-containing compounds
Class
Alkaloids
Sub-class
Purine and pyrimidine alkaloids

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"]

Spectra

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
Cocoa beanCocoa and cocoa products PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
Green teaTeas and herbal teas PublicationsShow
GuaranaBeverages, Non-alcoholic PublicationsShow
MateBeverages, Non-alcoholic PublicationsShow
Roasted coffeeCoffee and coffee products PublicationsShow
TeaTeas and herbal teas PublicationsShow

Food Sources of its Precursor(s)

No food source information available of its precursor(s)

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeine 1,3,7-Trimethyluric acidhumanblood, urinehost metabolismNot AvailableNot AvailableNot AvailableC8H10N4O3210.075290198 Detailed Intervention Studies Publications
Caffeine 1-methylxanthinehumanblood, urinehost metabolismNot AvailableNot AvailableNot AvailableC6H6N4O2166.049075449 Detailed Intervention Studies Publications

Inter-Individual Variations Metabolism

No inter-individual variations available

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