Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2018-05-29 00:29:07 UTC
Primary IDFDB000453
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheophylline
DescriptionTheophylline, also known as uniphyl or aerolate, 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. Theophylline is an extremely weak basic (essentially neutral) compound (based on its pKa). Theophylline is a bitter tasting compound. Theophylline is found, on average, in the highest concentration in cocoa beans and tea. Theophylline has also been detected, but not quantified in, a few different foods, such as arabica coffee, lemons, and pummelo. This could make theophylline a potential biomarker for the consumption of these foods. Theophylline is a potentially toxic compound.
CAS Number58-55-9
Structure
Thumb
Synonyms
SynonymSource
1,3-Dimethyl-7H-purine-2,6-dioneChEBI
1,3-DimethylxanthineChEBI
ElixophyllinChEBI
RespbidChEBI
Theo-durChEBI
TheolairChEBI
TheophyllinChEBI
Theophylline anhydrousChEBI
UniphylChEBI
Quibron-tKegg
Theo-24Kegg
Theodur gKegg
AccurbronHMDB
Acet-theocinHMDB
AerolateHMDB
Aerolate IIIHMDB
Aerolate SRHMDB
AminophyllineHMDB
AquaphyllinHMDB
ArmophyllineHMDB
AsbronHMDB
AsmaxHMDB
AustynHMDB
BronkodylHMDB
Bronkodyl SRHMDB
Choledyl saHMDB
Constant-THMDB
DiphyllinHMDB
DoraphyllinHMDB
DuraphylHMDB
Dyspne-inhalHMDB
ElixexHMDB
ElixiconHMDB
ElixominHMDB
Elixophyllin SRHMDB
ElixophyllineHMDB
EuphyllineHMDB
EuphylongHMDB
LabidHMDB
LanophyllinHMDB
LiquophyllineHMDB
LiquoriceHMDB
MaphyllineHMDB
MedaphyllinHMDB
NuelinHMDB
OptiphyllinHMDB
ParkophyllinHMDB
PseudotheophyllineHMDB
Quibron t/srHMDB
Quibron-t/srHMDB
Slo-bidHMDB
Slo-phyllinHMDB
SolosinHMDB
Somophyllin-CRTHMDB
Somophyllin-DFHMDB
Somophyllin-THMDB
Spophyllin retardHMDB
SustaireHMDB
SynophylateHMDB
Synophylate-l.a. cenulesHMDB
T-PhylHMDB
TefaminHMDB
TeofilinaHMDB
TeofyllaminHMDB
TeolairHMDB
TheacitinHMDB
Theal tabl.HMDB
Theal tabletsHMDB
Theo-dur-sprinkleHMDB
TheobidHMDB
Theobid jr.HMDB
TheochronHMDB
TheocinHMDB
Theoclair-SRHMDB
Theoclear 80HMDB
Theoclear l.a.-130HMDB
Theoclear laHMDB
Theoclear-200HMDB
Theoclear-80HMDB
TheocontinHMDB
TheodelHMDB
TheofolHMDB
TheogradHMDB
Theolair-SRHMDB
TheolixHMDB
TheolixirHMDB
Theona pHMDB
TheophylHMDB
Theophyl-225HMDB
Theophyl-SRHMDB
TheophylineHMDB
Theophylline-SRHMDB
Theostat 80HMDB
TheoventHMDB
Uni-durHMDB
UnifylHMDB
UniphyllinHMDB
XanthiumHMDB
XantiventHMDB
AerobinHMDB
BronchoparatHMDB
Glycine theophyllinateHMDB
Nuelin s.a.HMDB
Slo phyllinHMDB
SloPhyllinHMDB
Somophyllin THMDB
Theo24HMDB
Theoconfin continuousHMDB
TheoniteHMDB
CT Arzneimittel brand OF theophylline sodium glycinateHMDB
Von CT, theoHMDB
Mundipharma brand OF theophylline sodium glycinateHMDB
Quibron T SRHMDB
Quibron T-SRHMDB
Sodium glycinate, theophyllineHMDB
Theo 24HMDB
Theophyllinate, glycineHMDB
Theophylline sodium glycinateHMDB
TheospanHMDB
UniphyllineHMDB
CT-Arzneimittel brand OF theophylline sodium glycinateHMDB
ConstantTHMDB
Fameasan brand OF theophylline sodium glycinateHMDB
LodraneHMDB
MonospanHMDB
Quibron TSRHMDB
TheodurHMDB
TheonHMDB
TheopekHMDB
TheostatHMDB
CT, Theo vonHMDB
Theo von CTHMDB
1,3 DimethylxanthineHMDB
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dioneHMDB
Afonilum retardHMDB
Anhydrous, theophyllineHMDB
Constant THMDB
Fujisawa brand OF theophylline sodium glycinateHMDB
Glycinate, theophylline sodiumHMDB
SomophyllinTHMDB
Theo durHMDB
1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurinebiospider
1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dionebiospider
1,3-Dimethyl-3,9-dihydro-1H-purine-2,6-dionebiospider
1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-biospider
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-biospider
2,6-Dihydroxy-1,3-dimethylpurinebiospider
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, 9CIdb_source
Aerolate srHMDB
Bronkodyl srHMDB
Constant-tHMDB
Elixophyllin srHMDB
Labophyllinebiospider
Mudranebiospider
Purine-2,6(1H,3H)-dione, 1,3-dimethyl-biospider
Slophyllinbiospider
Somophyllin-crtHMDB
Somophyllin-dfHMDB
Somophyllin-tHMDB
T-phylHMDB
Teonovadb_source
Theoclair-srHMDB
Theokinbiospider
Theolair-srHMDB
Theona PHMDB
Theophyl-srHMDB
Theophylline-srHMDB
Xanthine, 1,3-dimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility22.9 g/LALOGPS
logP-0.26ALOGPS
logP-0.77ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8N4O2
IUPAC name1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChI KeyZFXYFBGIUFBOJW-UHFFFAOYSA-N
Isomeric SMILESCN1C2=C(NC=N2)C(=O)N(C)C1=O
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
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen 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 - Experimental
    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 264°DFC
    Boiling PointNot Available
    Experimental Water Solubility7.36 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
    Experimental logP-0.02HANSCH,C ET AL. (1995)
    Experimental pKapKa2 8.6 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f79-6970000000-224461ad62a44dbdf860JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-7900000000-a08735d528e738752429JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-d0882f7d959c726e7623JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9700000000-8d0e1898a6571fbca10aJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-6970000000-224461ad62a44dbdf860JSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fka-4900000000-878cab6882fd80efba3bJSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-0092516012d6a2a93b31JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-4900000000-dcf52c18a6996f412b1aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9000000000-09089337909892ef44cbJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001j-7900000000-a08735d528e738752429JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-001i-0900000000-d0882f7d959c726e7623JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-c4943571126a44bb9e5aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bc12ce29acd02fa749b8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03k9-0900000000-d63f60043f186fbb9bc0JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-070l-4900000000-d293ab2fa6199dbaf97aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-05ru-9400000000-dde4775588d52c83806fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-556e382f583d610ef1f0JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-89e34f5158856ba33469JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03k9-0900000000-65a6897d72954e875b00JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-070l-4900000000-df16604bd6c40cee8f24JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-05r3-9500000000-39a721dcecc86ed95507JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-1900000000-e67ff7ef9a955b90eb3fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-3900000000-1870952d98dbba22ace8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-7900000000-dc0e9606776c43a7823fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014j-9300000000-2c4c6490dda3ed3b563fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-26a6c0c23a465afdcde1JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-1900000000-b11ca3441bb29fef1906JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-9400000000-63726fe0b49a9dc6ba7eJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9100000000-139f765bc9b5855960c6JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-88b5cb393b960973ac64JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00yi-9000000000-1ebbddce3c7133972546JSpectraViewer | MoNA
    MSMass Spectrum (Electron Ionization)splash10-00lr-9500000000-2c8464c2fe84464c207fJSpectraViewer | MoNA
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID2068
    ChEMBL IDCHEMBL190
    KEGG Compound IDC07130
    Pubchem Compound ID2153
    Pubchem Substance IDNot Available
    ChEBI ID28177
    Phenol-Explorer IDNot Available
    DrugBank IDDB00277
    HMDB IDHMDB01889
    CRC / DFC (Dictionary of Food Compounds) IDBCK73-S:BCK73-S
    EAFUS IDNot Available
    Dr. Duke IDTHEOPHYLLINE| DIMETHYLXANTHINE
    BIGG IDNot Available
    KNApSAcK IDC00001510
    HET IDTEP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDTheophylline
    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
    allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
    anti apneic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti asthmatic49167 A drug used to treat asthma.DUKE
    anti bradyarrhythmic38070 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
    anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti cellulitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
    anti emphysemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.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
    cardiovascular38070 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 inhibitor35222 A substance that diminishes the rate of a chemical reaction.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
    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
    diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
    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
    hypertensiveDUKE
    hyperuricemicDUKE
    hypoglycemic35526 A drug which lowers the blood glucose level.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
    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
    prostaglandin secretorDUKE
    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
    vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
    Enzymes
    NameGene NameUniProt ID
    Adenosine deaminaseADAP00813
    Adenosine receptor A1ADORA1P30542
    Adenosine receptor A2aADORA2AP29274
    Adenosine receptor A2bADORA2BP29275
    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— 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.