FComEx: 1,3-Dimethyluric acid (PC000501)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:58 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000501

FoodDB Record

FDB022712

Chemical Information

Name

1,3-Dimethyluric acid

Description

1,3-Dimethyluric acid is a product of theophylline metabolism in man. 1,3-Dimethyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). 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. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. 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. (PMID: 11712316, 15833286, 3506820, 15013152, 4039734) [HMDB]

CAS Number

944-73-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,3-Dimethylurate	hmdb
1,3-Dimethyluric acid	hmdb
Oxytheophylline	hmdb

Chemical Formula

C7H8N4O3

IUPAC name

1,3-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

InChI Identifier

InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)

InChI Key

OTSBKHHWSQYEHK-UHFFFAOYSA-N

Isomeric SMILES

CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O

Average Molecular Weight

196.1634

Monoisotopic Molecular Weight

196.059640142

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents