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Showing Compound 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
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dioneChEBI
3,7-Dimethylpurine-2,6-dioneChEBI
3,7-DimethylxanthineChEBI
TheobrominChEBI
TeobrominHMDB
2,6-Dihydroxy-3,7-dimethyl-purineHMDB
3,7-Dimethyl-xanthineHMDB
DiurobromineHMDB
1H-Purine-2,6-dione, 3, 7-dihydro-3,7-dimethyl-biospider
1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-biospider
1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI)biospider
2,6-Dihydroxy-3,7-dimethylpurinebiospider
3-7-DIMETHYLXANTHINEbiospider
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 9CIdb_source
3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dionebiospider
3,7-dimethylpurine-2,6-dionebiospider
FEMA 3591db_source
Santheosedb_source
Theobromine [ban]biospider
Theobrominumbiospider
Theosalvosebiospider
Theostenebiospider
Thesaldb_source
Thesodatebiospider
Xanthine, 3,7-dimethyl-biospider
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 that suppresses appetite, reducing food intake. Its biological role involves regulating hunger and satiety signals. Therapeutically, anorexics are used to treat obesity and weight-related disorders, promoting weight loss and improving metabolic health. Key medical uses include managing exogenous obesity and related conditions, such as diabetes and hypertension.DUKE
    Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
    Anti cellulitic52217 An agent that reduces the appearance of cellulite, improving skin texture and tone. It enhances blood flow, breaks down fat cells, and strengthens connective tissue, commonly used in cosmetic and dermatological treatments to minimize dimpling and orange peel skin.DUKE
    ArteriodilatorAn agent that dilates arteries, increasing blood flow to or from the heart, used therapeutically to manage conditions like hypertension, heart failure, and angina, improving cardiac output and reducing blood pressure.DUKE
    Bronchodilator35523 An agent that relaxes airway muscles, increasing airflow to the lungs. It reduces bronchospasm, commonly used in managing asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders to improve breathing and relieve symptoms.DUKE
    cAMP inhibitor35222 An agent that blocks the activity of cyclic adenosine monophosphate (cAMP), a key signaling molecule. It reduces intracellular cAMP levels, modulating various biological processes. Therapeutically, cAMP inhibitors are used to treat conditions like asthma, cancer, and cardiovascular diseases by regulating cell signaling pathways and inflammation.DUKE
    cAMP-phosphodiesterase inhibitor23924 An agent that blocks the breakdown of cyclic adenosine monophosphate (cAMP), increasing its levels and enhancing cellular signaling. Therapeutically, it is used to treat respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD), as well as certain cardiovascular conditions.DUKE
    Cardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.DUKE
    cGMP-phosphodiesterase inhibitor23924 An agent that blocks the breakdown of cyclic guanosine monophosphate (cGMP), increasing its levels. It relaxes smooth muscle, dilates blood vessels, and improves cardiac function. Therapeutically used to treat erectile dysfunction, pulmonary hypertension, and heart failure, improving exercise tolerance and quality of life.DUKE
    Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
    Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
    EmeticAn agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures.DUKE
    Fetotoxic52209 An agent that is toxic to the fetus, causing harm or developmental issues during pregnancy. Its biological role is to induce fetal damage, and it has no therapeutic applications. Key medical uses include serving as a warning or contraindication for certain medications or substances during pregnancy to prevent fetal harm.DUKE
    Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
    Myocardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac function. It plays a biological role in increasing cardiac output and reducing symptoms of heart failure. Therapeutically, myocardiotonics are used to manage conditions like cardiomyopathy, heart failure, and coronary artery disease, improving overall cardiac performance.DUKE
    MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
    MyostimulantAn agent that stimulates an increase in the rhythm and amplitude of smooth muscle movement, playing a biological role in enhancing muscle contraction. Therapeutically, it is used to treat gastrointestinal disorders, such as constipation, and other conditions characterized by reduced muscle activity, like urinary retention.DUKE
    Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
    StimulantAn agent that enhances alertness, wakefulness, and physical activity by increasing brain activity. Therapeutically, it is used to treat attention deficit hyperactivity disorder (ADHD), narcolepsy, and certain cases of depression, improving focus, attention, and overall mental performance.DUKE
    Teratogenic50905 An agent that causes abnormal fetal development, disrupting embryonic growth and leading to birth defects. Its biological role is associated with developmental toxicity, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.DUKE
    Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.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.