CHEBI:62208 - 3-methyl-7H-xanthine

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ChEBI Name 3-methyl-7H-xanthine
ChEBI ID CHEBI:62208
ChEBI ASCII Name 3-methyl-7H-xanthine
Definition A 3-methylxanthine tautomer where the imidazole proton is located at the 7-position.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6349064, eMolecules:975955, eMolecules:489521, ZINC000004685854
Download Molfile XML SDF
Formula C6H6N4O2
Net Charge 0
Average Mass 166.13740
Monoisotopic Mass 166.04908
InChI InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)
InChIKey GMSNIKWWOQHZGF-UHFFFAOYSA-N
SMILES Cn1c2nc[nH]c2c(=O)[nH]c1=O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
(via 3-methylxanthine )
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
(via 3-methylxanthine )
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
(via 3-methylxanthine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-methyl-7H-xanthine (CHEBI:62208) has role metabolite (CHEBI:25212)
3-methyl-7H-xanthine (CHEBI:62208) is a 3-methylxanthine (CHEBI:62205)
3-methyl-7H-xanthine (CHEBI:62208) is tautomer of 3-methyl-9H-xanthine (CHEBI:62207)
Incoming 3-methyl-9H-xanthine (CHEBI:62207) is tautomer of 3-methyl-7H-xanthine (CHEBI:62208)
IUPAC Name
3-methyl-3,7-dihydro-1H-purine-2,6-dione
Synonyms Sources
3,7-dihydro-3-methyl-1H-purine-2,6-dione ChEBI
3-methyl-3,7(9)-dihydro-purine-2,6-dione ChEBI
3-methylxanthine UniProt
3-methylxanthine ChEBI
N1-demethyltheophylline ChEBI
Manual Xrefs Databases
3-METHYLXANTHINE MetaCyc
C16357 KEGG COMPOUND
HMDB0001886 HMDB
View more database links
Registry Numbers Types Sources
1076-22-8 CAS Registry Number KEGG COMPOUND
180944 Reaxys Registry Number Reaxys
Citations
Lee SW, Zhao L, Pardi A, Xia T (2010)
Ultrafast dynamics show that the theophylline and 3-methylxanthine aptamers employ a conformational capture mechanism for binding their ligands.
Biochemistry 49, 2943-2951 [PubMed:20214401]
[show Abstract]
Georgopoulou E, Mermelekas G, Karena E, Frillingos S (2010)
Purine substrate recognition by the nucleobase-ascorbate transporter signature motif in the YgfO xanthine permease: ASN-325 binds and ALA-323 senses substrate.
The Journal of biological chemistry 285, 19422-19433 [PubMed:20406814]
[show Abstract]
Guerreiro S, Toulorge D, Hirsch E, Marien M, Sokoloff P, Michel PP (2008)
Paraxanthine, the primary metabolite of caffeine, provides protection against dopaminergic cell death via stimulation of ryanodine receptor channels.
Molecular pharmacology 74, 980-989 [PubMed:18621927]
[show Abstract]
Geraets L, Moonen HJ, Wouters EF, Bast A, Hageman GJ (2006)
Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations.
Biochemical pharmacology 72, 902-910 [PubMed:16870158]
[show Abstract]
Morimoto T, Kotegawa T, Tsutsumi K, Ohtani Y, Imai H, Nakano S (2004)
Effect of St. John's wort on the pharmacokinetics of theophylline in healthy volunteers.
Journal of clinical pharmacology 44, 95-101 [PubMed:14681347]
[show Abstract]
Yao C, Kunze KL, Kharasch ED, Wang Y, Trager WF, Ragueneau I, Levy RH (2001)
Fluvoxamine-theophylline interaction: gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2.
Clinical pharmacology and therapeutics 70, 415-424 [PubMed:11719727]
[show Abstract]
Cavallaro RA, Filocamo L, Galuppi A, Galione A, Brufani M, Genazzani AA (1999)
Potentiation of cADPR-induced Ca(2+)-release by methylxanthine analogues.
Journal of medicinal chemistry 42, 2527-2534 [PubMed:10411473]
[show Abstract]
Niki Y, Itokawa K, Okazaki O (1998)
Effects of DU-6859a, a new quinolone antimicrobial, on theophylline metabolism in in vitro and in vivo studies.
Antimicrobial agents and chemotherapy 42, 1751-1755 [PubMed:9661016]
[show Abstract]
Chappe V, Mettey Y, Vierfond JM, Hanrahan JW, Gola M, Verrier B, Becq F (1998)
Structural basis for specificity and potency of xanthine derivatives as activators of the CFTR chloride channel.
British journal of pharmacology 123, 683-693 [PubMed:9517388]
[show Abstract]
Liu W, Meissner G (1997)
Structure-activity relationship of xanthines and skeletal muscle ryanodine receptor/Ca2+ release channel.
Pharmacology 54, 135-143 [PubMed:9127436]
[show Abstract]
Ogiso T, Iwaki M, Uno S (1995)
Inhibition kinetics of theophylline metabolism by mexiletine and its metabolites.
Biological & pharmaceutical bulletin 18, 75-81 [PubMed:7735255]
[show Abstract]
Last Modified
23 October 2015