Record Information
Version1.0
Creation date2010-04-08 22:11:47 UTC
Update date2019-11-26 03:11:29 UTC
Primary IDFDB015351
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,3,7,9-Tetramethyluric acid
DescriptionIsolated from tea Temurin is a methyl derivative of uric acid, found occasionally in human urine. Temurin 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. (PMID: 11712316, 15833286, 3506820, 15013152). 1,3,7,9-Tetramethyluric acid is found in cupuaçu and tea.
CAS Number2309-49-1
Structure
Thumb
Synonyms
SynonymSource
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
9-TetramethylateGenerator
9-Tetramethylic acidGenerator
Temurinbiospider
Uric acid, 1,3,7,9-tetramethyl-biospider
Uric acid, 1,3,7,9-tetramethyl- (8CI)biospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H12N4O3
IUPAC nametetramethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
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
Isomeric SMILESCN1C(=O)N(C)C2=C1N(C)C(=O)N(C)C2=O
Average Molecular Weight224.2166
Monoisotopic Molecular Weight224.09094027
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 48.21%; H 5.39%; N 24.99%; O 21.41%DFC
Melting PointMp 228°DFC
Boiling PointNot Available
Experimental Water Solubility25 mg/mL at 20 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,3,7,9-Tetramethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1910000000-620bbdc27e2d2ab3fa6fSpectrum
Predicted GC-MS1,3,7,9-Tetramethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8e9f489ece941b1ce61cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0950000000-342e6c57156137ef747dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-76be8ee71d5baf16b79cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-8ba7d307c874a65578f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0490000000-0fcaaaabdf4b0807a3efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-3900000000-40d235f6bb5475c84b8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-e02bcb3c0c3edf199294Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0390000000-a1803341d3d60eeb3370Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-8259fb7d643d26f28becSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-579c7f6492ff0d502c20Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0910000000-ff3114d0e44ee51de61dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0670-1900000000-526309eb3fb97359b08eSpectrum
NMRNot Available
ChemSpider ID67862
ChEMBL IDCHEMBL143715
KEGG Compound IDNot Available
Pubchem Compound ID75324
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04328
CRC / DFC (Dictionary of Food Compounds) IDJZR60-K:JZR65-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00034312
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.