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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:32 UTC |
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Update Date | 2020-11-09 23:17:11 UTC |
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HMDB ID | HMDB0003099 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-Methyluric acid |
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Description | 1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via 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 superfamily, 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 , 9890610 ). |
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Structure | |
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Synonyms | Value | Source |
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1-Methylate | Generator | 1-Methylic acid | Generator | 1-Methylurate | HMDB |
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Chemical Formula | C6H6N4O3 |
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Average Molecular Weight | 182.1368 |
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Monoisotopic Molecular Weight | 182.043990078 |
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IUPAC Name | 1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione |
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Traditional Name | 1-methyluric acid |
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CAS Registry Number | 708-79-2 |
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SMILES | CN1C(=O)NC2=C(NC(=O)N2)C1=O |
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InChI Identifier | InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12) |
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InChI Key | QFDRTQONISXGJA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | Xanthines |
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Alternative Parents | |
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Substituents | - Xanthine
- 6-oxopurine
- Purinone
- Alkaloid or derivatives
- Pyrimidone
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Lactam
- Urea
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5 mg/mL | Not Available | LogP | -0.57 | GASPARI,F & BONATI,M (1987) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0far-2900000000-7c88ba8c892ca8263473 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0900000000-f2e42cd67ce1106bed63 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-0900000000-9fd2304504c5787dc255 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-9000000000-6069b457c0c038edb8df | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0006-0900000000-f47eba015e7f8d9f21a7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-001i-0900000000-26da10b11bacabae0d00 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-001i-0900000000-dceee0216914a6ad0349 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-001r-0900000000-cb9d81f2cc810b6a1bf6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-0019-2900000000-79ddb513e243e4fd1054 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 10V, negative | splash10-001a-7900000000-aeb7c72625ab71bbfcb3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-000i-0900000000-72f91c756d76768ecc23 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-004i-9000000000-0ae8d2338f48c17984cd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-001i-9400000000-943dd572fd686e87913d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-03di-0109000000-cf0f38f1f9c792f0404d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-03di-0309000000-9a8aaf68c144b67fbc6e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-01q9-0905000000-d40f59a74d4b8cc4e1d6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-001i-0901000000-265af2cad1ab697d3249 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-001i-0900000000-2b4e4dd83c0bad2269ae | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-001i-0900000000-c37839583f5e4e15cc46 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, negative | splash10-001i-0900000000-6254efb7ddc081f6fd0c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-9fb7b528d968cab88bd3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0059-1900000000-eb2d1569b5bdfeef979a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000w-9300000000-065aa3463c121bf31312 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1900000000-62dd716e79c8fa6f5ee0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3900000000-bf85a8ad5b7719f36aba | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-7db60439b29417bbbe0d | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | - Amniotic Fluid
- Blood
- Feces
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Amniotic Fluid | Detected and Quantified | 0.51 +/- 0.044 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 13.95 +/- 10.65 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 25.20 +/- 13.5 umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Urine | Detected and Quantified | 7.04 +/- 1.57 umol/mmol creatinine | Adult (>18 years old) | Both | Canavan disease | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal adenoma | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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- Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023107 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 62926 |
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KEGG Compound ID | C16359 |
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BioCyc ID | CPD-14119 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 2821 |
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PubChem Compound | 69726 |
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PDB ID | Not Available |
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ChEBI ID | 68441 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000410 |
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References |
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Synthesis Reference | Prusse, August. Synthesis of methylated uric acids according to Behrend and Roosen. Ann. (1925), 441 203-15. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Tateishi T, Asoh M, Yamaguchi A, Yoda T, Okano YJ, Koitabashi Y, Kobayashi S: Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Pediatr Res. 1999 Jan;45(1):66-70. [PubMed:9890610 ]
- Nakano K, Assenza SP, Brown PR: Reversed-phase liquid chromatographic investigation of UV-absorbing low-molecular-weight compounds in saliva. J Chromatogr. 1982 Dec 10;233:51-60. [PubMed:7161362 ]
- Grygiel JJ, Wing LM, Farkas J, Birkett DJ: Effects of allopurinol on theophylline metabolism and clearance. Clin Pharmacol Ther. 1979 Nov;26(5):660-7. [PubMed:498708 ]
- Knoppert DC, Spino M, Beck R, Thiessen JJ, MacLeod SM: Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Clin Pharmacol Ther. 1988 Sep;44(3):254-64. [PubMed:3046811 ]
- Kilbane AJ, Silbart LK, Manis M, Beitins IZ, Weber WW: Human N-acetylation genotype determination with urinary caffeine metabolites. Clin Pharmacol Ther. 1990 Apr;47(4):470-7. [PubMed:2328555 ]
- 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 ]
- Miller CA, Slusher LB, Vesell ES: Polymorphism of theophylline metabolism in man. J Clin Invest. 1985 May;75(5):1415-25. [PubMed:4039734 ]
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