1,3,7-Trimethyluric acid (CHEM021740)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:11:21 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021740
Identification
Common Name1,3,7-Trimethyluric acid
ClassSmall Molecule
DescriptionAn oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8, and the nitrogens at positions 1, 3, and 7 are substituted by methyl groups. It is a metabolite of caffeine.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,7-Trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneChEBI
1,3,7-TrimethylurateChEBI
7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trioneChEBI
8-OxocaffeineChEBI
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 FormulaC8H10N4O3
Average Molecular Mass210.190 g/mol
Monoisotopic Mass210.075 g/mol
CAS Registry Number5415-44-1
IUPAC Name1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,3,7-trimethyluric acid
SMILESCN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
InChI IdentifierInChI=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 KeyBYXCFUMGEBZDDI-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.32 m³·mol⁻¹ChemAxon
Polarizability19.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-7ceff209b1b0d4f92cf0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0900000000-5316637dfdcce19f087aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0imj-3930000000-0593f0aaec496efc7696Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000f-9500000000-fb28fd8903d55811b0a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-0910000000-eca560d36d14fb72dfe9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-6d4b9f5e8e42f3040e5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000l-7900000000-2ba0d4f876fceab5182fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000f-9700000000-a42f3584a2bad7add22dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052o-1920000000-53b778bbd3181f2ed83aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000l-3900000000-4305cd286c077e521079Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0690000000-62dc7eb029289b61c3b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000f-0900000000-3eb9fdcfd2e67d0f4e2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-f438ad2b70b2e9735643Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-42add8be62bbafed200cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2930000000-2855ca36942d5e8f069eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9200000000-708fd95bbe618c2ace7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f524Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002123
FooDB IDFDB022854
Phenol Explorer IDNot Available
KNApSAcK IDC00051957
BiGG IDNot Available
BioCyc IDCPD-12480
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1,3,7-Trimethyluric_acid
Chemspider ID71754
ChEBI ID691622
PubChem Compound ID79437
Kegg Compound IDC16361
YMDB IDNot Available
ECMDB IDM2MDB004651
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10076532
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11712316
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15013152
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15537072
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15833286
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17981969
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26967371
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=31123759
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31910660
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=32193380
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=32841636
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=3506820
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6888171
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9061462
15.
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC6818814
17. 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.
18. 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.
19. 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.
20. 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.