| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:37 -0600 |
| Update Date |
2013-06-10 10:36:54 -0600 |
| HMDB ID |
HMDB02123 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
1,3,7-Trimethyluric acid |
| Description |
1,3,7-Trimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,3,7-Trimethyluracil 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1,3, 7-Trimethyluric acid
- 1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione
- 1,3,7-Trimethylurate
- 2,6,8-Trihydroxy-1,3,7-trimethylpurine
- 7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trione
- 8-Hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
- 8-Oxy-caffeine
- Trimethyl uric acid
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| Chemical Formula |
C8H10N4O3 |
| Average Molecular Weight |
210.19 |
| Monoisotopic Molecular Weight |
210.075290206 |
| IUPAC Name |
1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione |
| Traditional IUPAC Name |
1,3,7-trimethyl uric acid |
| CAS Registry Number |
5415-44-1 |
| SMILES |
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C |
| InChI Identifier |
InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14) |
| InChI Key |
BYXCFUMGEBZDDI-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Imidazopyrimidines |
| Sub Class |
Purines and Purine Derivatives |
| Other Descriptors |
- Organic Compounds
- Purine alkaloids(KEGG)
- Purinones
- a small molecule(Cyc)
- oxopurine(ChEBI)
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| Substituents |
- Imidazole
- Pyrimidine
- Pyrimidone
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| Direct Parent |
Xanthines |
| Ontology |
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| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
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| Application |
Not Available
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| Cellular locations |
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| Physical Properties |
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| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
5.5 mg/mL at 15 °C |
Not Available |
| LogP |
-0.37 |
GASPARI,F & BONATI,M (1987) |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
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| Blood |
Expected but not Quantified |
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Not Applicable |
Not Available |
Not Available |
Normal
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| Urine |
Detected and Quantified |
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0.63 (0.63-0.93) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal
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| Abnormal Concentrations |
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| Urine |
Detected and Quantified |
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2.19 (0.0-5.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Asthma
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| Associated Disorders and Diseases |
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| Disease References |
| Asthma |
|---|
- Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72.
Pubmed: 15537072
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| Associated OMIM IDs |
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| External Links |
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| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022854 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
71754 |
| KEGG Compound ID |
C16361 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB02123 |
| Metagene Link |
HMDB02123 |
| METLIN ID |
Not Available |
| PubChem Compound |
79437 |
| PDB ID |
Not Available |
| ChEBI ID |
691622 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
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| General References |
- Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49.
Pubmed: 11712316
- Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35.
Pubmed: 15833286
- Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18.
Pubmed: 3506820
- Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89.
Pubmed: 15013152
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Normal
