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Theobromine

PubChem CID: 5429

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Compound Synonyms theobromine, 83-67-0, 3,7-Dimethylxanthine, Diurobromine, Theosalvose, Santheose, Teobromin, Theostene, Thesodate, Thesal, 3,7-dimethylpurine-2,6-dione, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, Theobromin, Xantheose, Xanthine, 3,7-dimethyl-, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, FEMA No. 3591, Theobrominum, Theobromine (natural), 2,6-Dihydroxy-3,7-dimethylpurine, SC 15090, 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-, NSC 5039, MFCD00022830, CCRIS 2350, BRN 0016464, HSDB 7332, UNII-OBD445WZ5P, NSC-5039, 519-41-5, EINECS 201-494-2, 2,6-Dihydroxy-3,7-dimethyl-purine, OBD445WZ5P, DTXSID9026132, CHEBI:28946, 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, CHEMBL1114, SC-15090, DTXCID506132, NSC5039, 5-26-13-00553 (Beilstein Handbook Reference), Theobromine (3,7-Dimethylxanthine), 3,7-dimethyl-1H-purine-2,6-dione, CAS-83-67-0, NCGC00016023-11, THEOBROMINE (IARC), THEOBROMINE [IARC], 3,7-Dimethyl-1H-purine-2,6(3H,7H)-dione, THEOBROMINE (MART.), THEOBROMINE [MART.], THEOBROMINE (EP IMPURITY), THEOBROMINE [EP IMPURITY], 7-Dimethylxanthine, PENTOXIFYLLINE IMPURITY A (EP IMPURITY), PENTOXIFYLLINE IMPURITY A [EP IMPURITY], SR-01000000069, Theobromine [INN:BAN:NF], 37T, Prestwick_1054, Theobromine(20%), 3,7-dimethylxanthin, Spectrum_000053, Theobromine (Standard), 3,7-Dimethyl-xanthine, Caffeine EP impurity D, THEOBROMINE [MI], Prestwick0_000874, Prestwick1_000874, Prestwick2_000874, Prestwick3_000874, Spectrum2_000985, Spectrum3_000279, Spectrum4_000403, Spectrum5_001387, Lopac-T-4500, THEOBROMINE [FHFI], THEOBROMINE [HSDB], THEOBROMINE [VANDF], THEOBROMINUM [HPUS], SCHEMBL3184, Theobromine, >=98.0%, 3,7-dimethyl-1,3,7-trihydropurine-2,6-dione, Lopac0_001187, BSPBio_000947, BSPBio_001758, KBioGR_000666, KBioSS_000433, THEOBROMINE [WHO-DD], MLS000028407, DivK1c_000611, SPECTRUM1500649, SPBio_001049, SPBio_002868, BPBio1_001043, Theobromine, analytical standard, HMS501O13, HY-N0138R, KBio1_000611, KBio2_000433, KBio2_003001, KBio2_005569, KBio3_001258, YAPQBXQYLJRXSA-UHFFFAOYSA-, NINDS_000611, HMS1570P09, HMS1921O13, HMS2092G04, HMS2097P09, HMS3263N15, HMS3714P09, Pharmakon1600-01500649, HY-N0138, Theobromine 0.1 mg/ml in Methanol, Theobromine, >=98.0% (HPLC), Tox21_110284, Tox21_300016, Tox21_501187, BBL034679, BDBM50014260, CCG-40078, NSC757407, PDSP1_001017, PDSP2_001001, s2368, STL419465, AKOS000121558, Tox21_110284_1, 5-26-13-00553 (Beilstein), CS-7972, DB01412, FT33795, LP01187, NSC-757407, SDCCGMLS-0002875.P003, SDCCGSBI-0051154.P004, IDI1_000611, NCGC00016023-01, NCGC00016023-02, NCGC00016023-03, NCGC00016023-04, NCGC00016023-05, NCGC00016023-06, NCGC00016023-07, NCGC00016023-08, NCGC00016023-09, NCGC00016023-10, NCGC00016023-12, NCGC00016023-13, NCGC00016023-14, NCGC00016023-15, NCGC00016023-17, NCGC00016023-18, NCGC00016023-26, NCGC00024123-03, NCGC00024123-04, NCGC00024123-05, NCGC00024123-06, NCGC00024123-07, NCGC00024123-08, NCGC00179030-01, NCGC00179030-02, NCGC00253943-01, NCGC00261872-01, WLN: T56 BN DN FNVMVJ B1 F1, AC-11381, AC-34381, AS-13904, DA-68137, SMR000058357, SY048379, SBI-0051154.P003, 1H-Purine-2, 3,7-dihydro-3,7-dimethyl-, AB00052141, EU-0101187, NS00009946, T0178, EN300-16609, purine-2,6(1H,3H)-dione, 3,7-dimethyl-, C07480, D71206, T 4500, AB00052141_12, Q206844, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #, SR-01000000069-2, SR-01000000069-4, SR-01000000069-7, SR-01000000069-8, SR-01000000069-9, BRD-K34888156-001-08-8, BRD-K34888156-001-11-2, BRD-K34888156-213-01-4, CAFFEINE MONOHYDRATE IMPURITY D [EP IMPURITY], CEC63CCA-3B4B-4F4F-92C1-1789DF3C880A, SR-01000000069-10, Z56347209, 1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI), Theobromine, European Pharmacopoeia (EP) Reference Standard, 3,7-DIMETHYLXANTHINE, 3,7-DIMETHYLPURINE-2,6-DIONE, Theobromine, Pharmaceutical Secondary Standard, Certified Reference Material, 201-494-2, InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 67.2
Hydrogen Bond Donor Count 1.0
Pfizer 3 75 Rule False
Scaffold Graph Level CC1CC(C)C2CCCC2C1
Np Classifier Class Purine alkaloids
Deep Smiles Cncncc5c=O)[nH]c=O)n6C
Heavy Atom Count 13.0
Pathway Kegg Map Id map00232
Classyfire Class Imidazopyrimidines
Description Constituent of tea leaves (Camellia thea), cocoa Theobroma cacao, cola nut (Cola acuminata) and guarana (Paullinia cupana), flavouring ingredient with a bitter taste 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9) -- Pubchem, As a methylated xanthine, theobromine is a potent Cyclic adenosine monophosphate (cAMP) phosphodiesterase inhibitor, this means that it helps prevent the enzyme phosphodiesterase from converting the active cAMP to an inactive form. cAMP works as a second messenger in many hormone- and neurotransmitter-controlled metabolic systems, such as the breakdown of glycogen. When the inactivation of cAMP is inhibited by a compound such as theobromine, the effects of the neurotransmitter or hormone which stimulated the production of cAMP are much longer lived. The net result is generally a stimulatory effect., As it is a myocardial stimulant as well as a vasodilator, it increases heartbeat, yet it also dilates blood vessels, causing a reduced blood pressure. However, a recent paper published suggested that the decrease in blood pressure may be caused by flavanols. Furthermore, its draining effect allows it to be used to treat cardiac failure, which can be caused by an excessive accumulation of fluid., Even without dietary intake, theobromine may occur in the body as it is a product of the human metabolism of caffeine which is metabolised in the liver into 10% theobromine, 4% theophylline, and 80% paraxanthine., In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. -- Wikipedia, It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. -- Wikipedia, Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine.Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". -- Wikipedia, Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus. -- Wikipedia, Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine, Theobromine is a water insoluble, crystalline, bitter powder, the colour has been listed as either white or colourless. It has a similar, but lesser, effect to caffeine, making it a lesser homologue. Theobromine is an isomer of theophylline as well as paraxanthine. Theobromine is categorized as a dimethyl xanthine, which means it is a xanthine with two methyl groups., Theobromine, also known as xantheose, is a bitter alkaloid of the cacao plant, found in chocolate, as well as in a number of chocolate-free foods made from theobromine sources including the leaves of the tea plant, the kola or cola nut, and acai berries[citation needed]. It is in the methylxanthine class of chemical compounds, which also includes the similar compounds theophylline and caffeine. (In caffeine, the only difference is that the NH group of theobromine is an N-CH3 group.) Despite its name, the compound contains no bromine ? theobromine is derived from Theobroma, the name of the genus of the cacao tree, (which itself is made up of the Greek roots theo ("God") and brosi ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds., While theobromine and caffeine are similar in that they are related alkaloids, theobromine is weaker in both its inhibition of cyclic nucleotide phosphodiesterases and its antagonism of adenosine receptors. Therefore, theobromine has a lesser impact on the human central nervous system than caffeine. However, theobromine stimulates the heart to a greater degree.[citation needed] While theobromine is not as addictive, it has been cited as possibly causing addiction to chocolate. Theobromine has also been identified as one of the compounds contributing to chocolate's reputed role as an aphrodisiac., it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. -- Wikipedia.
Scaffold Graph Node Level OC1NC(O)C2NCNC2N1
Classyfire Subclass Purines and purine derivatives
Isotope Atom Count 0.0
Molecular Complexity 267.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Enzyme Uniprot Id P30542, P29274
Uniprot Id P47989, Q07343, P05181, P05177, P30542, P29274, P25099, P30543, Q01453, P28482, P08482, P08684, Q96KQ7, O15648, P83916, Q13526, P19793, Q12809, O94782, O42275, P81908, Q9NPD5, Q9Y6L6, P15289, n.a., P0DTD1
Iupac Name 3,7-dimethylpurine-2,6-dione
Prediction Hob 1.0
Class Imidazopyrimidines
Veber Rule True
Classyfire Superclass Organoheterocyclic compounds
Target Id NPT796, NPT282, NPT109
Xlogp -0.8
Superclass Alkaloids and derivatives
Subclass Purines and purine derivatives
Gsk 4 400 Rule True
Molecular Formula C7H8N4O2
Scaffold Graph Node Bond Level O=c1[nH]c(=O)c2[nH]cnc2[nH]1
Prediction Swissadme 0.0
Inchi Key YAPQBXQYLJRXSA-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.2857142857142857
Logs -2.504
Rotatable Bond Count 0.0
State Solid
Logd -0.239
Synonyms 1H-Purine-2,6-dione, 3, 7-dihydro-3,7-dimethyl-, 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-, 1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI), 2,6-Dihydroxy-3,7-dimethyl-purine, 2,6-Dihydroxy-3,7-dimethylpurine, 3-7-DIMETHYLXANTHINE, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 9CI, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, 3,7-Dimethyl-xanthine, 3,7-dimethylpurine-2,6-dione, 3,7-Dimethylxanthine, Diurobromine, FEMA 3591, Santheose, Teobromin, Theobromin, Theobromine [ban], Theobrominum, Theosalvose, Theostene, Thesal, Thesodate, Xanthine, 3,7-dimethyl-, 3,7-Dimethylpurine-2,6-dione, theobromin, theobromine
Substituent Name Alkaloid or derivatives, Xanthine, Purinone, 6-oxopurine, Purine, Imidazopyrimidine, Pyrimidone, Pyrimidine, N-substituted imidazole, Heteroaromatic compound, Vinylogous amide, Imidazole, Azole, Urea, Lactam, Azacycle, Organoheterocyclic compound, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Aromatic heteropolycyclic compound
Esol Class Very soluble
Functional Groups c=O, c[nH]c, cn(c)C, cnc
Compound Name Theobromine
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 180.065
Formal Charge 0.0
Monoisotopic Mass 180.065
Hydrogen Bond Acceptor Count 3.0
Molecular Weight 180.16
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -1.9040430923076919
Inchi 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)
Smiles CN1C=NC2=C1C(=O)NC(=O)N2C
Nring 2.0
Np Classifier Biosynthetic Pathway Alkaloids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Taxonomy Direct Parent Xanthines
Np Classifier Superclass Pseudoalkaloids

  • 1. Outgoing r'ship FOUND_IN to/from Acanthophyllum Elatius (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Aconitum Pseudohuiliense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Aconitum Sachalinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Alstonia Deplanchei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Asteriscus Graveolens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Baccharis Megapotamica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Boronia Coerulescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Cacalia Bicolor (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Camellia Japonica (Plant) Rel Props:Reference:ISBN:9788172360481
  • 10. Outgoing r'ship FOUND_IN to/from Camellia Sinensis (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Centrosema Pascuorum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Ceratozamia Fuscoviridis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Citrus Glauca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Citrus Limon (Plant) Rel Props:Source_db:fooddb_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Citrus Maxima (Plant) Rel Props:Source_db:fooddb_chem_all
  • 16. Outgoing r'ship FOUND_IN to/from Codium Decorticatum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Coffea Arabica (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Coffea Benghalensis (Plant) Rel Props:Reference:ISBN:9788172362133
  • 19. Outgoing r'ship FOUND_IN to/from Coffea Canephora (Plant) Rel Props:Reference:ISBN:9788172362133
  • 20. Outgoing r'ship FOUND_IN to/from Cola Acuminata (Plant) Rel Props:Reference:ISBN:9788172360481; ISBN:9788172362133
  • 21. Outgoing r'ship FOUND_IN to/from Cola Nitida (Plant) Rel Props:Reference:ISBN:9788172362133
  • 22. Outgoing r'ship FOUND_IN to/from Critonia Quadrangularis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Erigeron Crispus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 24. Outgoing r'ship FOUND_IN to/from Eupatorium Gracile (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Ficus Simplicissima (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 26. Outgoing r'ship FOUND_IN to/from Flemingia Congesta (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 27. Outgoing r'ship FOUND_IN to/from Haplophyllum Dauricum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 28. Outgoing r'ship FOUND_IN to/from Honorius Nutans (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Ilex Aquifolium (Plant) Rel Props:Reference:ISBN:9780387706375
  • 30. Outgoing r'ship FOUND_IN to/from Ilex Paraguariensis (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/11190409
  • 31. Outgoing r'ship FOUND_IN to/from Ilex Purpurea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Iryanthera Coriacea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 33. Outgoing r'ship FOUND_IN to/from Marrubium Supinum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Melochia Tomentosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 35. Outgoing r'ship FOUND_IN to/from Metalasia Bolusii (Plant) Rel Props:Source_db:npass_chem_all
  • 36. Outgoing r'ship FOUND_IN to/from Orthosphenia Mexicana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 37. Outgoing r'ship FOUND_IN to/from Oxyanthus Speciosus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 38. Outgoing r'ship FOUND_IN to/from Quercus Dentata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 39. Outgoing r'ship FOUND_IN to/from Relhania Pumila (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 40. Outgoing r'ship FOUND_IN to/from Rheum Tanguticum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 41. Outgoing r'ship FOUND_IN to/from Rubia Oncotricha (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 42. Outgoing r'ship FOUND_IN to/from Senecio Latifolius (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 43. Outgoing r'ship FOUND_IN to/from Senecio Rivularis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 44. Outgoing r'ship FOUND_IN to/from Solanum Elaeagnifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 45. Outgoing r'ship FOUND_IN to/from Stevia Mercedensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 46. Outgoing r'ship FOUND_IN to/from Strychnos Tabascana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 47. Outgoing r'ship FOUND_IN to/from Styrax Perkinsiae (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 48. Outgoing r'ship FOUND_IN to/from Swinglea Glutinosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 49. Outgoing r'ship FOUND_IN to/from Theobroma Cacao (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 50. Outgoing r'ship FOUND_IN to/from Thuja Standishii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 51. Outgoing r'ship FOUND_IN to/from Verbesina Rupestris (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
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