1,3,7,9-Tetramethyluric acid (CHEM030179)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:42:31 UTC
Update Date2016-11-09 01:19:01 UTC
Accession NumberCHEM030179
Identification
Common Name1,3,7,9-Tetramethyluric acid
ClassSmall Molecule
DescriptionAn oxopurine that is uric acid in which the hydrogens at positions 1,3,7 and 9 are replaced by methyl groups. It is a purine alkaloid that is found in Chinese tea known as kucha (Camellia assamica var. kucha) and exhibits anti-inflammatory and analgesic properties.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Ba 2750ChEBI
TeaCrineChEBI
TemorineChEBI
Tetramethyl uric acidChEBI
Tetramethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneChEBI
Tetramethyluric acidChEBI
TheacrineChEBI
Tetramethyl urateGenerator
TetramethylateGenerator
Tetramethylic acidGenerator
1,3,7,9-Tetramethyluric acidMeSH
1379-Tetramethyluric acidChEMBL, HMDB
1379-TetramethylateGenerator, HMDB
1379-Tetramethylic acidGenerator, HMDB
1,3,7, 9-Tetramethyluric acidHMDB
1,3,7,9-Tetramethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
1,3,7,9-TetramethylateGenerator
1,3,7,9-Tetramethylic acidGenerator
Chemical FormulaC9H12N4O3
Average Molecular Mass224.217 g/mol
Monoisotopic Mass224.091 g/mol
CAS Registry Number2309-49-1
IUPAC Nametetramethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Nametetramethyluric acid
SMILESCN1C(=O)N(C)C2=C1N(C)C(=O)N(C)C2=O
InChI IdentifierInChI=1S/C9H12N4O3/c1-10-5-6(11(2)8(10)15)12(3)9(16)13(4)7(5)14/h1-4H3
InChI KeyQGDOQULISIQFHQ-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 Solubility58 g/LALOGPS
logP-0.15ALOGPS
logP-0.65ChemAxon
logS-0.59ALOGPS
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.17 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.22 m³·mol⁻¹ChemAxon
Polarizability21.82 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, Positivesplash10-014i-1910000000-620bbdc27e2d2ab3fa6fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8e9f489ece941b1ce61cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0950000000-342e6c57156137ef747dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-76be8ee71d5baf16b79cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-8ba7d307c874a65578f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0490000000-0fcaaaabdf4b0807a3efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-3900000000-40d235f6bb5475c84b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-e02bcb3c0c3edf199294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0390000000-a1803341d3d60eeb3370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-8259fb7d643d26f28becSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-579c7f6492ff0d502c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0910000000-ff3114d0e44ee51de61dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0670-1900000000-526309eb3fb97359b08eSpectrum
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
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 IDHMDB0004328
FooDB IDFDB015351
Phenol Explorer IDNot Available
KNApSAcK IDC00034312
BiGG IDNot Available
BioCyc IDCPD-12505
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTheacrine
Chemspider ID67862
ChEBI ID139388
PubChem Compound ID75324
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12009315
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1383710
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14977550
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20227468
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22579816
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23678853
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23724689
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26610558
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26766930
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27164220
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27635133
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28864241
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28875060
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29727630
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31172618
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=31298401
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=32193380
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=32286351
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=32546720
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=32707370
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=32730889
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=32829142
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=331090
24. 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.
25. 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.
26. 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.
27. 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.