7-Methylxanthine (BioCAD00000005417)

blood feces urine kidney liver plant natural products

Metabolite Card

Formula: C6H6N4O2 (166.0491)
SMILES: CN1C=NC2=C1C(=O)NC(=O)N2

Synonyms [en]

7-methylxanthine; Heteroxanthine; 3,7-Dihydro-7-methyl-1H-purine-2,6-dione; 7-Methylxanthin; Heteroxanthin; 7-methyl-3,7-dihydro-1H-purine-2,6-dione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

7-Methylxanthine. 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: BioCAD00000005417). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites, including 7-methylxanthine. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. (PMID:11712316, 15833286, 3506820, 15013152).

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 552-62-5
  • PubChem: 68374
  • ChEBI: ChEBI:48991
  • HMDB: HMDB0001991
  • HMDB: HMDB01991
  • KEGG: C16353
  • BioCyc: 7-METHYLXANTHINE
  • NCBI MeSH: 7-methylxanthine
  • Wikipedia: 7-Methylxanthine
  • Wikipedia: Xanthine
  • RefMet: RM0033054
  • MoNA: HMDB0001991_ms_ms_1932
  • MoNA: HMDB0001991_ms_ms_1933
  • MoNA: HMDB0001991_ms_ms_1934
  • MoNA: MoNA010866
  • MoNA: MoNA010867
  • MoNA: MoNA010868
  • MoNA: MoNA010869
  • MoNA: RP016301
  • MoNA: RP016302
  • MoNA: RP016303
  • Metlin: METLIN_58075
  • Coconut NaturalProduct: CNP0325938.0
  • Coconut NaturalProduct: CNP0578661.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07918 3.2.2.25 7-methylxanthosine ribohydrolase
KEGG:R07919 2.1.1.159 S-adenosyl-L-methionine:7-methylxanthine N3-methyltransferase
KEGG:R07922 C00019 + C16353<=>C00021 + C13747
KEGG:R07957 1.14.13.178 paraxanthine:oxygen oxidoreductase (N1-demethylating)
KEGG:R07958 1.14.13.178 paraxanthine: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:R07965 1.14.13.128 7-methylxanthine:oxygen oxidoreductase (demethylating)
KEGG:R07966 1.14.13.128 7-methylxanthine:oxygen oxidoreductase (demethylating)
KEGG:R07979 1.17.3.2 7-methylxanthine:oxygen oxidoreductase
Rhea:RHEA:10881 3.2.2.25 7-methylxanthosine + H2O => 7-methylxanthine + D-ribose + H+
Rhea:RHEA:10882 3.2.2.25 7-methylxanthine + D-ribose + H+ => 7-methylxanthosine + H2O
Rhea:RHEA:10883 3.2.2.25 7-methylxanthosine + H2O <=> 7-methylxanthine + D-ribose + 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:30308 1.14.13.128 7-methylxanthine + NADPH + O2 + H+ => xanthine + formaldehyde + NADP+ + H2O
Rhea:RHEA:30309 1.14.13.128 xanthine + formaldehyde + NADP+ + H2O => 7-methylxanthine + NADPH + O2 + H+
Rhea:RHEA:30310 1.14.13.128 7-methylxanthine + NADPH + O2 + H+ <=> xanthine + formaldehyde + NADP+ + H2O
Rhea:RHEA:30312 1.14.13.128 7-methylxanthine + NADH + O2 + H+ => xanthine + formaldehyde + NAD+ + H2O
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Organism Source

Taxonomy Source

  1. Camellia assamica [ncbi taxid: ]
  2. Camellia irrawadiensisia [ncbi taxid: ]
  3. Camellia kissi [ncbi taxid: ]
  4. Camellia ptilophylla [ncbi taxid: 319931]
  5. Camellia sinensis [ncbi taxid: 4442]
  6. Camellia taliensis [ncbi taxid: 182317]
  7. Camellia toliensis [ncbi taxid: ]
  8. Cammellia assamica var.kucha [ncbi taxid: ]
  9. Citrus maxima [ncbi taxid: 37334]
  10. Coffea arabica [ncbi taxid: 13443]
  11. Coffea canephora [ncbi taxid: 49390]
  12. Coffea dewevrei [ncbi taxid: ]
  13. Coffea eugeniodes [ncbi taxid: ]
  14. Coffea kianjavatensis [ncbi taxid: 339904]
  15. Coffea liberica [ncbi taxid: 49373]
  16. Coffea racemosa [ncbi taxid: 49377]
  17. Coffea salvatrix [ncbi taxid: 49380]
  18. Cola sp. [ncbi taxid: ]
  19. Herreania sp. [ncbi taxid: ]
  20. Ilex paraguariensis [ncbi taxid: 185542]
  21. Paullinia cupana [ncbi taxid: 392747]
  22. Theobroma cacao [ncbi taxid: 3641]
  23. Theobroma grandiflorum [ncbi taxid: 108881]
  24. Homo sapiens [ncbi taxid: 9606]
  25. Mus musculus [ncbi taxid: 10090]
  26. Theobroma cacao [ncbi taxid: 3641]

Pathway Synthetic

pathway id name
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-5038 caffeine biosynthesis II (via paraxanthine)
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-5038 caffeine biosynthesis II (via paraxanthine)
PlantCyc:PLANT_PWY-5037 caffeine biosynthesis I
PlantCyc:COCOA_PWY-5038 caffeine biosynthesis II (via paraxanthine)
PlantCyc:PLANT_PWY-5039 theobromine biosynthesis I
PlantCyc:TEA_PWY-5037 caffeine biosynthesis I
PlantCyc:TEA_PWY-5038 caffeine biosynthesis II (via paraxanthine)
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