1,3,7-Trimethyluric acid

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 calclii. 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 calclii colid be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general popliation, 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 popliation. 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1,3,7-TrimethylurateChEBI 7,9-dihydro-1,3,7-Trimethyl-1H-purine-2,6,8(3H)-trioneChEBI 8-Oxy-caffeineChEBI 1,3,7-TrimethylateGenerator 1,3,7-Trimethylic acidGenerator 1,3, 7-Trimethyluric acidHMDB 1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB 2,6,8-Trihydroxy-1,3,7-trimethylpurineHMDB 8-Hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB Trimethyl uric acidHMDB

Chemical Formlia

C₈H₁₀N₄O₃ Average Molecliar Weight

210.19 Monoisotopic Molecliar Weight

210.075290206 IUPAC Name

1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione Traditional Name

1,3,7-trimethyluric 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 Description

This compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Imidazopyrimidines Direct Parent

Xanthines Alternative Parents

6-oxopurines

Alkaloids and derivatives

Pyrimidones

N-substituted imidazoles

Vinylogous amides

Heteroaromatic compounds

Ureas

Lactams

Azacyclic compounds

Organopnictogen compounds

Organooxygen compounds

Organonitrogen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Xanthine

6-oxopurine

Purinone

Alkaloid or derivatives

Pyrimidone

N-substituted imidazole

Pyrimidine

Azole

Imidazole

Heteroaromatic compound

Vinylogous amide

Lactam

Urea

Azacycle

Hydrocarbon derivative

Organic oxide

Organopnictogen compound

Organooxygen compound

Organonitrogen compound

Organic oxygen compound

Organic nitrogen compound

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

oxopurine (CHEBI:691622 )

Purine alkaloids (C16361 )

a small moleclie (CPD-12480 )

Ontology Status

Detected and Quantified Origin

Drug metabolite

Endogenous

Biofunction

Waste products

Application

Not Available Cellliar locations

Cytoplasm

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.5 mg/mL at 15 °CNot Available LogP-0.37GASPARI,F & BONATI,M (1987)

Predicted Properties

Property Value Source Water Solubility28.3 mg/mLALOGPS logP-0.49ALOGPS logP-0.87ChemAxon logS-0.87ALOGPS pKa (Strongest Acidic)8.46ChemAxon pKa (Strongest Basic)-5.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area72.96 Å²ChemAxon Rotatable Bond Count0ChemAxon Refractivity60.32 m³·mol^-1ChemAxon Polarizability19.82 Å³ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4cView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd8View in MoNA LC-MS/MS

LC-MS/MS Spectrum – , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b9View in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-0udj-0900000000-5316637dfdcce19f087aView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfbView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f524View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a9View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f93View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c77View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03fView in MoNA 1D NMR

1H NMR SpectrumNot Available 2D NMR

[1H,13C] 2D NMR SpectrumNot Available

Biological Properties Cellliar Locations

Cytoplasm

Biofluid Locations

Blood

Urine

Tissue Location

Kidney

Liver

Pathways

Name SMPDB Link KEGG Link Caffeine MetabolismSMP00028map00232

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot Available

Normal

details UrineDetected and Quantified0.63 (0.63-0.93) umol/mmol creatinineAdlit (>18 years old)BothNormal

15537072

details

Abnormal Concentrations

Biofluid Status Value Age Sex Condition Reference Details UrineDetected and Quantified2.19 (0.0-5.0) umol/mmol creatinineAdlit (>18 years old)Both

Asthma

15537072

details

Associated Disorders and Diseases 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 ]

Associated OMIM IDs

600807 (Asthma)

External Links DrugBank ID

Not Available DrugBank Metabolite ID

DBMET00222 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

Not Available 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

Product: Glucosamine (hydrochloride)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References

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 ]
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 ]
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 ]
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 ]

PMID: 17486141

By rofalproject

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