Theobromine (BioCAD00000018439)

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Metabolite Card

Formula: C7H8N4O2 (180.0647)
SMILES: CN1C=NC2=C1C(O)=NC(=O)N2C

Synonyms [en]

theobromine; 3,7-Dimethylxanthine; 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione; 3,7-dimethylpurine-2,6-dione; Diurobromine; Teobromin

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Theobromine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000018439). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Theobromine, or 3,7-Dimethylxanthine, is 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. 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". 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. Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus.

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 519-41-5
  • CAS Registry Number: 66407-26-9
  • CAS Registry Number: 83-67-0
  • PubChem: 5429
  • ChEBI: ChEBI:28946
  • HMDB: HMDB0002825
  • KEGG: C07480
  • BioCyc: 3-7-DIMETHYLXANTHINE
  • NCBI MeSH: Theobromine
  • Wikipedia: Theobromine
  • DrugBank: DB01412
  • RefMet: RM0159435
  • MoNA: BAF_UVA_POS000173
  • MoNA: BAF_UVA_POS001185
  • MoNA: BAF_UVA_POS001186
  • MoNA: BAF_UVA_POS001187
  • MoNA: BML01074
  • MoNA: BML01082
  • MoNA: BML82245
  • MoNA: BML82247
  • MoNA: Bruker_HCD_library001095
  • MoNA: CCMSLIB00000424791
  • MoNA: CCMSLIB00000578038
  • MoNA: CCMSLIB00000578285
  • MoNA: CCMSLIB00000579214
  • MoNA: CCMSLIB00003142439
  • MoNA: CCMSLIB00004684345
  • MoNA: CCMSLIB00005464198
  • MoNA: CCMSLIB00005720480
  • MoNA: CO000476
  • MoNA: CO000477
  • MoNA: CO000478
  • MoNA: CO000479
  • MoNA: CO000480
  • MoNA: EMBL-MCF_spec61644
  • MoNA: HMDB0002825_c_ms_1729
  • MoNA: HMDB0002825_ms_ms_2143
  • MoNA: HMDB0002825_ms_ms_2144
  • MoNA: HMDB0002825_ms_ms_2145
  • MoNA: JP002808
  • MoNA: KO004122
  • MoNA: KO004123
  • MoNA: KO004124
  • MoNA: KO004125
  • MoNA: KO004126
  • MoNA: LU094101
  • MoNA: LU094102
  • MoNA: LU094103
  • MoNA: LU094104
  • MoNA: LU094105
  • MoNA: LU094106
  • MoNA: LU094151
  • MoNA: LU094152
  • MoNA: LU094153
  • MoNA: LU094154
  • MoNA: LU094155
  • MoNA: LU094156
  • MoNA: MoNA002109
  • MoNA: MoNA002110
  • MoNA: MoNA002113
  • MoNA: MoNA010077
  • MoNA: MoNA010078
  • MoNA: MoNA010079
  • MoNA: MoNA010080
  • MoNA: MoNA010081
  • MoNA: MoNA010082
  • MoNA: MoNA011356
  • MoNA: MoNA011357
  • MoNA: MoNA011358
  • MoNA: MoNA011359
  • MoNA: MoNA016802
  • MoNA: MoNA023976
  • MoNA: MoNA032264
  • MoNA: MoNA032265
  • MoNA: MoNA032266
  • MoNA: MoNA036172
  • MoNA: MoNA036174
  • MoNA: MoNA036175
  • MoNA: MoNA037224
  • MoNA: MoNA038605
  • MoNA: PM018501
  • MoNA: PM018502
  • MoNA: PM018503
  • MoNA: PM018504
  • MoNA: RP012201
  • MoNA: RP012202
  • MoNA: RP012203
  • MoNA: VF-NPL-LTQ007750
  • MoNA: VF-NPL-LTQ007751
  • MoNA: VF-NPL-LTQ007752
  • MoNA: VF-NPL-QEHF028126
  • MoNA: VF-NPL-QEHF028127
  • MoNA: VF-NPL-QEHF028128
  • MoNA: VF-NPL-QEHF028129
  • MoNA: VF-NPL-QEHF028130
  • MoNA: VF-NPL-QEHF028131
  • MoNA: VF-NPL-QEHF028132
  • MoNA: VF-NPL-QEHF028133
  • MoNA: VF-NPL-QEHF028134
  • MoNA: VF-NPL-QEHF028135
  • MoNA: VF-NPL-QEHF028136
  • MoNA: VF-NPL-QEHF028137
  • MoNA: VF-NPL-QEHF028138
  • MoNA: VF-NPL-QEHF028139
  • MoNA: VF-NPL-QEHF028140
  • Metlin: METLIN_1456
  • Coconut NaturalProduct: CNP0017726.0
  • Coconut NaturalProduct: CNP0108793.0
  • Coconut NaturalProduct: CNP0328305.0
  • Coconut NaturalProduct: CNP0519862.0
  • Coconut NaturalProduct: CNP0568853.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07919 2.1.1.159 S-adenosyl-L-methionine:7-methylxanthine N3-methyltransferase
KEGG:R07920 2.1.1.160 S-adenosyl-L-methionine:3,7-dimethylxanthine N1-methyltransferase
KEGG:R07955 1.14.13.178 caffeine:oxygen oxidoreductase (N1-demethylating)
KEGG:R07956 1.14.13.178 caffeine:oxygen oxidoreductase (N1-demethylating)
KEGG:R07961 1.14.13.179 theobromine:oxygen oxidoreductase (N3-demethylating)
KEGG:R07962 1.14.13.179 theobromine:oxygen oxidoreductase (N3-demethylating)
KEGG:R07963 1.13.12.- C07480 + C00004 + C00080 + C00007<=>C16357 + C00003 + C00067 + C00001
KEGG:R07964 1.13.12.- C07480 + C00005 + C00080 + C00007<=>C16357 + C00006 + C00067 + C00001
KEGG:R07978 1.17.3.2 3,7-dimethylxanthine:oxygen oxidoreductase
Rhea:RHEA:20945 2.1.1.160 theobromine + S-adenosyl-L-methionine => caffeine + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:20946 2.1.1.160 caffeine + S-adenosyl-L-homocysteine + H+ => theobromine + S-adenosyl-L-methionine
Rhea:RHEA:20947 2.1.1.160 theobromine + S-adenosyl-L-methionine <=> caffeine + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:24605 2.1.1.159 7-methylxanthine + S-adenosyl-L-methionine => theobromine + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:24606 2.1.1.159 theobromine + S-adenosyl-L-homocysteine + H+ => 7-methylxanthine + S-adenosyl-L-methionine
Rhea:RHEA:24607 2.1.1.159 7-methylxanthine + S-adenosyl-L-methionine <=> theobromine + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:30320 1.14.13.179 theobromine + NADH + O2 + H+ => 7-methylxanthine + formaldehyde + NAD+ + H2O
Rhea:RHEA:30321 1.14.13.179 7-methylxanthine + formaldehyde + NAD+ + H2O => theobromine + NADH + O2 + H+
Rhea:RHEA:30322 1.14.13.179 theobromine + NADH + O2 + H+ <=> 7-methylxanthine + formaldehyde + NAD+ + H2O
Rhea:RHEA:36268 1.14.13.178 caffeine + NADH + O2 + H+ => theobromine + formaldehyde + NAD+ + H2O
Rhea:RHEA:36269 1.14.13.178 theobromine + formaldehyde + NAD+ + H2O => caffeine + NADH + O2 + H+
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Organism Source

Taxonomy Source

  1. Zyzzya fuliginosa [ncbi taxid: 1346156]
  2. Camellia irawadiensis [ncbi taxid: ]
  3. Camellia irrawadiensis [ncbi taxid: 153142]
  4. Camellia ptilophylla [ncbi taxid: 319931]
  5. Camellia sinensis [ncbi taxid: 4442]
  6. Camellia sinensis (L.) O. [ncbi taxid: ]
  7. Camellia taliensis [ncbi taxid: 182317]
  8. Camellia thea [ncbi taxid: ]
  9. Ceratonia siliqua [ncbi taxid: 20340]
  10. Citrullus lanatus [ncbi taxid: 3654]
  11. Citrus limon [ncbi taxid: ]
  12. Citrus maxima [ncbi taxid: 37334]
  13. Citrus paradisi [ncbi taxid: ]
  14. Coffea arabica L. [ncbi taxid: ]
  15. Coffea canephora [ncbi taxid: 49390]
  16. Coffea dewevrei [ncbi taxid: ]
  17. Coffea eugeniodes [ncbi taxid: ]
  18. Coffea kianjavatensis [ncbi taxid: 339904]
  19. Coffea liberica [ncbi taxid: 49373]
  20. Coffea racemosa [ncbi taxid: 49377]
  21. Coffea salvatrix [ncbi taxid: 49380]
  22. Cola acuminata [ncbi taxid: 93760]
  23. Cola sp. [ncbi taxid: ]
  24. Herreania sp. [ncbi taxid: ]
  25. Ilex aquifolium L. [ncbi taxid: ]
  26. Ilex paraguariensis A.St.-Hil. [ncbi taxid: ]
  27. Ilex perado [ncbi taxid: 53209]
  28. Ilex verticillata (L.) A. Gray [ncbi taxid: ]
  29. Paullinia cupana [ncbi taxid: 392747]
  30. Paullinia pachycarpa [ncbi taxid: 557021]
  31. Paullinia trifoliata [ncbi taxid: ]
  32. Paullinia yoco [ncbi taxid: ]
  33. Pseudopiptadenia leptostachya [ncbi taxid: ]
  34. Scurrula atropurpurea [ncbi taxid: 1146880]
  35. Scurrura atropurpurea [ncbi taxid: ]
  36. Theobroma cacao [ncbi taxid: 3641]
  37. Theobroma cacao L. [ncbi taxid: ]
  38. Theobroma grandiflorum [ncbi taxid: 108881]
  39. Acanthophyllum elatius [ncbi taxid: 2603713]
  40. Aconitum pseudohuiliense [ncbi taxid: ]
  41. Aconitum sachalinense [ncbi taxid: 50880]
  42. Alcyonium molle [ncbi taxid: ]
  43. Alstonia deplanchei [ncbi taxid: ]
  44. Amanita cokeri [ncbi taxid: 87323]
  45. Aplophyllum popovii [ncbi taxid: ]
  46. Asteriscus graveolens [ncbi taxid: 73976]
  47. Atalantia roxburghiana [ncbi taxid: 159027]
  48. Baccharis megapotamica [ncbi taxid: 2707461]
  49. Bombus muscorum [ncbi taxid: 203813]
  50. Boronia coerulescens [ncbi taxid: ]
  51. Cacalia bicolor [ncbi taxid: ]
  52. Camellia sinensis [ncbi taxid: 4442]
  53. Centaurea diluta [ncbi taxid: 41531]
  54. Centrosema pascuorum [ncbi taxid: 1983288]
  55. Ceratozamia fuscoviridis [ncbi taxid: 1115353]
  56. Cereus candicans [ncbi taxid: ]
  57. Citrus glauca [ncbi taxid: 76963]
  58. Codium decorticatum [ncbi taxid: 414126]
  59. Coffea arabica [ncbi taxid: 13443]
  60. Critonia quadrangularis [ncbi taxid: 1475404]
  61. Cryptotermes cynocephalus [ncbi taxid: 105781]
  62. Dacrydium fonki [ncbi taxid: ]
  63. Erigeron crispus [ncbi taxid: ]
  64. Eupatorium gracile [ncbi taxid: ]
  65. Ficus simplicissima [ncbi taxid: 1822162]
  66. Flemingia congesta [ncbi taxid: 2730189]
  67. Fomes cajanderi [ncbi taxid: ]
  68. Haplophyllum dauricum [ncbi taxid: 452773]
  69. Homo sapiens [ncbi taxid: 9606]
  70. Honorius nutans [ncbi taxid: 535968]
  71. Ilex purpurea [ncbi taxid: 185544]
  72. Iryanthera coriacea [ncbi taxid: ]
  73. Lecanora planaica [ncbi taxid: ]
  74. Marrubium supinum [ncbi taxid: 155230]
  75. Melochia tomentosa [ncbi taxid: 1127084]
  76. Metalasia bolusii [ncbi taxid: ]
  77. Mus musculus [ncbi taxid: 10090]
  78. Orthosphenia mexicana [ncbi taxid: 123438]
  79. Oxyanthus speciosus [ncbi taxid: 353880]
  80. Perezia carpholepis [ncbi taxid: ]
  81. Pseudocyphellaria impressa [ncbi taxid: ]
  82. Quercus dentata [ncbi taxid: 103484]
  83. Relhania pumila [ncbi taxid: ]
  84. Rheum tanguticum [ncbi taxid: 137226]
  85. Rhinoceros sondaicus [ncbi taxid: 102233]
  86. Rubia oncotricha [ncbi taxid: 715731]
  87. Salacia prinoides [ncbi taxid: ]
  88. Salmonella enterica subsp. enterica serovar typhimurium [ncbi taxid: 90371]
  89. Senecio latifolius [ncbi taxid: 422353]
  90. Senecio rivularis [ncbi taxid: ]
  91. Sinularia maxima [ncbi taxid: ]
  92. Solanum elaeagnifolium [ncbi taxid: 115664]
  93. Stevia mercedensis [ncbi taxid: ]
  94. Streptomyces hachijoensis [ncbi taxid: 66899]
  95. Streptomyces xantholiticus [ncbi taxid: 68285]
  96. Strychnos tabascana [ncbi taxid: 1040932]
  97. Styrax perkinsiae [ncbi taxid: 153547]
  98. Swinglea glutinosa [ncbi taxid: 159066]
  99. Symploca hydnoides [ncbi taxid: 207924]
  100. Theobroma cacao [ncbi taxid: 3641]
  101. Thuja standishii [ncbi taxid: 89194]
  102. Verbesina rupestris [ncbi taxid: ]
  103. Zanthoxylum usambarense [ncbi taxid: 2562172]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5040 theobromine biosynthesis II (via xanthine)
BioCyc:META_PWY-5039 theobromine biosynthesis I
BioCyc:META_PWY-5037 caffeine biosynthesis I
BioCyc:META_PWY-6632 caffeine degradation IV (bacteria, via demethylation and oxidation)
BioCyc:META_PWY-6538 caffeine degradation III (bacteria, via demethylation)
PlantCyc:COCOA_PWY-5039 theobromine biosynthesis I
PlantCyc:COCOA_PWY-5037 caffeine biosynthesis I
PlantCyc:PLANT_PWY-5037 caffeine biosynthesis I
PlantCyc:PLANT_PWY-5039 theobromine biosynthesis I
PlantCyc:PLANT_PWY-5040 theobromine biosynthesis II (via xanthine)
PlantCyc:TEA_PWY-5037 caffeine biosynthesis I
PlantCyc:TEA_PWY-5039 theobromine biosynthesis I
WikiPathways:WP3633 Caffeine and theobromine metabolism
PathBank:SMP0000028 Caffeine Metabolism
PathBank:SMP0063475 Caffeine Metabolism
PathBank:SMP0063604 Caffeine Metabolism
PathBank:SMP0087288 Caffeine Metabolism
PathBank:SMP0087186 Caffeine Metabolism
View All Pathways