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Caffeine (FDB002100)

Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2019-11-26 02:57:00 UTC
Primary IDFDB002100
Secondary Accession Numbers
  • FDB017732
Chemical Information
FooDB NameCaffeine
DescriptionCaffeine, also known as coffein or mateina, 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. Caffeine is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeine is a bitter and odorless tasting compound. Caffeine is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and tea and in a lower concentration in energy drinks, ice cream cones, and other candies. Caffeine has also been detected, but not quantified in, several different foods, such as longans, cornbread, whiskies, american shad, and highbush blueberries. This could make caffeine a potential biomarker for the consumption of these foods. Caffeine is a potentially toxic compound.
CAS Number58-08-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
  • Purinone
  • 6-oxopurine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Foods
  • Cocoa and cocoa products

    • Beverages:

    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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-052f-8900000000-68b5e9aa3404fb3d8d3a2014-09-20View Spectrum
    GC-MSCaffeine, 0 TMS, GC-MS Spectrumsplash10-0536-3900000000-a9e112713ffae6dabdaaSpectrum
    GC-MSCaffeine, 0 TMS, GC-MS Spectrumsplash10-0536-2900000000-8cdcd005b2e7622a02a3Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-052f-0900000000-f1084acfddb240696073Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-05nf-6900000000-8670a644cee5d9de78d4Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0536-3900000000-4430852b279a72e34822Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-51898e93480e848d7da1Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-2aed5d425b6a95add5dbSpectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0a4l-4900000000-3ff72dace6687d242f1fSpectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-2ba1fae6e27c7b836984Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-fd859aeb416e320d6379Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0536-3900000000-a9e112713ffae6dabdaaSpectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0536-2900000000-8cdcd005b2e7622a02a3Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-052f-0900000000-f1084acfddb240696073Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-05nf-6900000000-8670a644cee5d9de78d4Spectrum
    GC-MSCaffeine, non-derivatized, GC-MS Spectrumsplash10-0536-3900000000-4430852b279a72e34822Spectrum
    Predicted GC-MSCaffeine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-0900000000-41f36d541d34d2088964Spectrum
    Predicted GC-MSCaffeine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0900000000-447fc72b2c709e2e18a92012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-5e3b29de16ad91c79fe02012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-d6f6c52ac36c8f25a5002012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-0900000000-cddd24399d942b1ac97c2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0002-0900000000-2aed5d425b6a95add5db2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a4l-4900000000-3ff72dace6687d242f1f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0006-1900000000-2ba1fae6e27c7b8369842012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-0002-0900000000-63b9ef42a3e8d59e99972012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0900000000-185b3d97d8857a0f269d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-0900000000-f8a0c0dd9f5c4a272eaf2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-1900000000-dd8e35226d0704aa657d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01x9-9800000000-70e3b0eb52481c39d1912012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9100000000-6d428a5571beb0e3fed42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-98bec16f898808c3de682012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0002-0900000000-b112e4e059e1ecf98c5f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00dr-0900000000-42c6f8fc7b924e9c64f32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-4900000000-a60a480f1340558740a22017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-695d910d49fc0beb1d542017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-094879886a2e72bf0c562017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-fa38c865089a3a05f2872017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000b-0900000000-0e82732a924c974dd0c82017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-bfc94c8091471847482b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-c8fcf16986c4948982032017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-3900000000-9569e0552abb7ebd145a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-3a924abd44877050c1c92017-09-14View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
    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
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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.