Showing Compound Card for Theobromine (CDB005294)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 10 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:28:45 UTC
Updated at2020-12-07 19:11:54 UTC
CannabisDB IDCDB005294
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Theobromine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC7H8N4O2
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0647
IUPAC Name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheobromine
CAS Registry Number83-67-0
SMILES
CN1C=NC2=C1C(O)=NC(=O)N2C
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point357 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 mg/mL at 25 °CNot Available
logP-0.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
cAMP-specific 3',5'-cyclic phosphodiesterase 4BPDE4B1p31Q07343 details
Adenosine receptor A1ADORA11q32.1P30542 details
Adenosine receptor A2aADORA2A22q11.23P29274 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
cAMP-specific 3',5'-cyclic phosphodiesterase 4BPDE4B1p31Q07343 details
Cytochrome P450 2E1CYP2E110q24.3-qterP05181 details
Cytochrome P450 1A2CYP1A215q24.1P05177 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Adenosine receptor A1ADORA11q32.1P30542 details
Adenosine receptor A2aADORA2A22q11.23P29274 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002825
DrugBank IDDB01412
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000455
KNApSAcK IDC00001509
Chemspider ID5236
KEGG Compound IDC07480
BioCyc ID3-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkTheobromine
METLIN ID1456
PubChem Compound5429
PDB IDNot Available
ChEBI ID28946
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Enzyme Details
2. cAMP-specific 3',5'-cyclic phosphodiesterase 4B
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:
PDE4B
Uniprot ID:
Q07343
Molecular weight:
64351.765
Enzyme Details
3. Adenosine receptor A1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
ADORA1
Uniprot ID:
P30542
Molecular weight:
36511.3
Enzyme Details
4. Adenosine receptor A2a
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
ADORA2A
Uniprot ID:
P29274
Molecular weight:
44706.9