Record Information
Version1.0
Creation date2015-05-07 18:46:52 UTC
Update date2019-11-27 17:44:44 UTC
Primary IDFDB030187
Secondary Accession Numbers
  • FDB022854
Chemical Information
FooDB Name1,3,7-trimethylurate
Description1,3,7-trimethyluric acid, also known as 8-oxy-caffeine or 137-trimethylate, is a member of the class of compounds known as xanthines. Xanthines are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 1,3,7-trimethyluric acid is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,3,7-trimethyluric acid can be found in a number of food items such as devilfish, allium (onion), cocoa bean, and epazote, which makes 1,3,7-trimethyluric acid a potential biomarker for the consumption of these food products. 1,3,7-trimethyluric acid can be found primarily in blood, feces, and urine, as well as in human kidney and liver tissues. In humans, 1,3,7-trimethyluric acid is involved in the caffeine metabolism. Moreover, 1,3,7-trimethyluric acid is found to be associated with asthma. 1,3,7-Trimethyluric acid, also referred to as trimethyluric acid and 8-oxy-caffeine, is a purine alkaloid that is produced in some plants and occurs as a minor metabolite of caffeine in humans. The enzymes that metabolize caffeine into 1,3,7-trimethyluric acid in humans include CYP1A2, CYP2E1, CYP2C8, CYP2C9, and CYP3A4 .
CAS Number5415-44-1
Structure
Thumb
Synonyms
SynonymSource
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H10N4O3
IUPAC name1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
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
Isomeric SMILESCN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
Average Molecular Weight210.19
Monoisotopic Molecular Weight210.075290206
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:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-7ceff209b1b0d4f92cf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0900000000-5316637dfdcce19f087aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f524View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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