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Theobromine (FDB000455)

Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2020-09-17 15:41:41 UTC
Primary IDFDB000455
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheobromine
DescriptionTheobromine, also known as diurobromine, 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. Theobromine is an extremely weak basic (essentially neutral) compound (based on its pKa). Theobromine is an isomer of theophylline, as well as paraxanthine. Theobromine exists in all living organisms, ranging from bacteria to humans. Within humans, theobromine participates in a number of enzymatic reactions. In particular, theobromine and formaldehyde can be biosynthesized from caffeine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In addition, theobromine can be converted into 3,7-dimethyluric acid through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, theobromine is involved in caffeine metabolism. Theobromine is a bitter tasting compound. Outside of the human body, Theobromine is found, on average, in the highest concentration within a few different foods, such as cocoa powders, chocolates, and cocoa beans and in a lower concentration in other candies, cakes, and soy milks. Theobromine has also been detected, but not quantified in, several different foods, such as hyacinth beans, oyster mushrooms, tamarinds, milk (other mammals), and watercress. This could make theobromine a potential biomarker for the consumption of these foods. Theobromine and caffeine are similar in that they are related alkaloids. A necropsy and toxicology report performed at the University of New Hampshire in 2015 confirmed they died of heart failure caused by theobromine after they consumed 41 kilograms (90 lb) of chocolate and doughnuts placed at the site as bait.
CAS Number83-67-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.76 g/LALOGPS
logP-0.78ALOGPS
logP-0.77ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H8N4O2
IUPAC name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChI KeyYAPQBXQYLJRXSA-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC2=C1C(=O)NC(=O)N2C
Average Molecular Weight180.164
Monoisotopic Molecular Weight180.06472552
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Foods
  • Cocoa and cocoa products

    • Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 46.67%; H 4.48%; N 31.10%; O 17.76%DFC
    Melting PointMp 351°DFC
    Boiling PointSubl. 290°DFC
    Experimental Water Solubility0.33 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
    Experimental logP-0.78HANSCH,C ET AL. (1995)
    Experimental pKapKa2 10 (25°)DFC
    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)splash10-001i-9700000000-770b2dc556ada7d97cae2015-03-01View Spectrum
    GC-MSTheobromine, 1 TMS, GC-MS Spectrumsplash10-0079-7980000000-efb14ee11aad17b6b4d2Spectrum
    GC-MSTheobromine, non-derivatized, GC-MS Spectrumsplash10-001i-6900000000-7d44855bbf11e559d96eSpectrum
    GC-MSTheobromine, non-derivatized, GC-MS Spectrumsplash10-0079-7980000000-efb14ee11aad17b6b4d2Spectrum
    Predicted GC-MSTheobromine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zgr-0900000000-87a73eda89d8ce593ee8Spectrum
    Predicted GC-MSTheobromine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-8d639c53ad9b2b8f508e2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-0d20b5fe9b93b113a29e2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-55968ca3e94ce5a05cfe2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-6900000000-7d44855bbf11e559d96e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-1900000000-1932568f11357ae32f552012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-2900000000-3918185c5a4afb18f11a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0910-5900000000-b590772083f824ea0fc62012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9400000000-c06ac99fd6e0c84d96532012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9100000000-3802e577174b5a4acced2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-02a9-2900000400-2ae0058f4f5f9fc23c012017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-004j-7900000000-54365e34320abc3c8f2e2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-599d34de0bc963388dc02017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-2900000000-8a0fd0cd87c35684d19f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0910-5900000000-b590772083f824ea0fc62017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9400000000-c06ac99fd6e0c84d96532017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9100000000-3802e577174b5a4acced2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b1202b5f491f2aaaf5422017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-0900000000-d58a783853c528b7d1262017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-8900000000-d9e4a4411ab0ed3620a02017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-3f82b9da0450b7ae12ae2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-235bf01d7d7435b9fe542017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9200000000-cb89e2e8ee405aba807d2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-fa072bef954a047da7f72017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0900000000-22f6a3f6049c3a9938782017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-afa55dfa675c3caec4f02017-06-28View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
    ChemSpider ID5236
    ChEMBL IDCHEMBL1114
    KEGG Compound IDC07480
    Pubchem Compound ID5429
    Pubchem Substance IDNot Available
    ChEBI ID28946
    Phenol-Explorer IDNot Available
    DrugBank IDDB01412
    HMDB IDHMDB02825
    CRC / DFC (Dictionary of Food Compounds) IDBCL39-R:BCL39-R
    EAFUS ID3651
    Dr. Duke IDTHEOBROMINE
    BIGG IDNot Available
    KNApSAcK IDC00001509
    HET ID37T
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDTheobromine
    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
    anorexic50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
    anti asthmatic49167 A drug used to treat asthma.DUKE
    anti cellulitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    arteriodilatorDUKE
    bronchodilator35523 An agent that causes an increase in the expansion of a bronchus or bronchial tubes.DUKE
    cAMP inhibitor35222 A substance that diminishes the rate of a chemical reaction.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
    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
    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
    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
    diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
    emeticDUKE
    fetotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    herbicide24527 A substance used to destroy plant pests.DUKE
    myocardiotonic38070 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
    myorelaxantDUKE
    myostimulantDUKE
    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
    stimulantDUKE
    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
    vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
    Enzymes
    NameGene NameUniProt ID
    Adenosine receptor A1ADORA1P30542
    Adenosine receptor A2aADORA2AP29274
    Pathways
    NameSMPDB LinkKEGG Link
    Caffeine MetabolismSMP00028 map00232
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    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.