Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2018-05-28 23:07:01 UTC
Primary IDFDB002100
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeine
DescriptionComponent of coffee beans (Coffea arabica), many other Coffea subspecies, chocolate (Theobroma cacao), tea (Camellia thea), kolanut (Cola acuminata) and several other Cola subspecies and several other plants. It is used in many cola-type beverages as a flavour enhancer. Caffeine is found in many foods, some of which are black cabbage, canola, jerusalem artichoke, and yellow bell pepper.
CAS Number58-08-2
Structure
Thumb
Synonyms
SynonymSource
1,3,7-Trimethyl-2,6-dioxopurineChEBI
1,3,7-Trimethylpurine-2,6-dioneChEBI
1,3,7-TrimethylxanthineChEBI
1-MethyltheobromineChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dionChEBI
7-MethyltheophyllineChEBI
Anhydrous caffeineChEBI
CafeinaChEBI
CafeineChEBI
CoffeinChEBI
GuaranineChEBI
KoffeinChEBI
MateinaChEBI
MethyltheobromineChEBI
TeinaChEBI
TheinChEBI
TheineChEBI
RespiaKegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
1-Methyl-theobromineHMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dioneHMDB
7-Methyl theophyllineHMDB
Anhydrous caffeine (JP15)HMDB
HycomineHMDB
LanorinalHMDB
MethyltheobromideHMDB
Methylxanthine theophyllineHMDB
Monohydrate caffeineHMDB
PropoxypheneHMDB
Merck dura brand OF caffeineHMDB
Thompson brand 1 OF caffeineHMDB
Bristol-myers squibb brand OF caffeineHMDB
CaffedrineHMDB
DexitacHMDB
Percoffedrinol NHMDB
Pierre fabre brand OF caffeineHMDB
Republic drug brand OF caffeineHMDB
Thompson brand 2 OF caffeineHMDB
VivarinHMDB
Coffeinum NHMDB
Coffeinum purrumHMDB
DurvitanHMDB
GlaxoSmithKline brand OF caffeineHMDB
No dozHMDB
PercutaféineHMDB
Quick-pepHMDB
Seid brand OF caffeineHMDB
Berlin-chemie brand OF caffeineHMDB
Passauer brand OF caffeineHMDB
Quick pepHMDB
QuickPepHMDB
1,3,7-Trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurinebiospider
3,7-dihydro-1,3,7-Trimethyl-1H-purin-2,6-dionChEBI
3,7-dihydro-1,3,7-Trimethyl-1H-purine-2,6-dioneHMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, 9CIdb_source
Anhydrous caffeine (jp15)HMDB
Caffeinbiospider
Cafipeldb_source
Coffeinedb_source
FEMA 2224db_source
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability18.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H10N4O2
IUPAC name1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI KeyRYYVLZVUVIJVGH-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC2=C1C(=O)N(C)C(=O)N2C
Average Molecular Weight194.1906
Monoisotopic Molecular Weight194.080375584
Classification
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 49.48%; H 5.19%; N 28.85%; O 16.48%DFC
Melting PointMp 236° (phase transition at 141°)DFC
Boiling PointNot Available
Experimental Water Solubility21.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.07HANSCH,C ET AL. (1995)
Experimental pKa10.4
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-3900000000-a9e112713ffae6dabdaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-2900000000-8cdcd005b2e7622a02a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052f-0900000000-f1084acfddb240696073View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e34822View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-51898e93480e848d7da1View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-fd859aeb416e320d6379View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0536-3900000000-a9e112713ffae6dabdaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0536-2900000000-8cdcd005b2e7622a02a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-0900000000-f1084acfddb240696073View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e34822View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0900000000-41f36d541d34d2088964View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0900000000-447fc72b2c709e2e18a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-5e3b29de16ad91c79fe0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-d6f6c52ac36c8f25a500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-0900000000-cddd24399d942b1ac97cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-0002-0900000000-63b9ef42a3e8d59e9997View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0900000000-185b3d97d8857a0f269dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-0900000000-f8a0c0dd9f5c4a272eafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-1900000000-dd8e35226d0704aa657dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01x9-9800000000-70e3b0eb52481c39d191View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9100000000-6d428a5571beb0e3fed4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-98bec16f898808c3de68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0002-0900000000-b112e4e059e1ecf98c5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00dr-0900000000-42c6f8fc7b924e9c64f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-4900000000-a60a480f1340558740a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-695d910d49fc0beb1d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-094879886a2e72bf0c56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-761710441aa2c1c3ac68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0900000000-c10af6eda9a9a4094715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-3900000000-141118b1a93b4d48b2d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c8bd8cccb7dd6c66bb42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-2c8c1760161edd358026View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5900000000-260de4a79007e853e4bbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-8900000000-68b5e9aa3404fb3d8d3aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID2424
ChEMBL IDCHEMBL113
KEGG Compound IDC07481
Pubchem Compound ID2519
Pubchem Substance IDNot Available
ChEBI ID27732
Phenol-Explorer IDNot Available
DrugBank IDDB00201
HMDB IDHMDB01847
CRC / DFC (Dictionary of Food Compounds) IDCFJ89-C:CFJ89-C
EAFUS ID441
Dr. Duke IDCAFFEINE
BIGG IDNot Available
KNApSAcK IDC00001492
HET IDCFF
Flavornet IDNot Available
GoodScent IDrw1014161
SuperScent IDNot Available
Wikipedia IDCaffeine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
(+)-inotropicDUKE
adenosine antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
analeptic35337 Any drug that enhances the activity of the central nervous system.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti apneic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti apoptoticDUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti emetic50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypotensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti narcoticDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti serotonergic48278 DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti vaccinia22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
arrhythmigenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
catabolicDUKE
cGMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cholereticDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
coronarydilatorDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
energizerDUKE
ergotamine enhancerDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hypertensiveDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
lypolyticDUKE
myorelaxantDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pyrogenicDUKE
respirastimulantDUKE
spasmogenicDUKE
stimulantDUKE
tachycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
serine/threonine kinase inhibitor50925 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.CHEBI
psychotropic35471 A loosely defined grouping of drugs that have effects on psychological function.CHEBI
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Adenosine receptor A1ADORA1P30542
Adenosine receptor A2aADORA2AP29274
Pathways
NameSMPDB LinkKEGG Link
Caffeine MetabolismSMP00028 map00232
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.