Record Information
Version1.0
Creation date2010-04-08 22:11:46 UTC
Update date2019-11-26 03:11:26 UTC
Primary IDFDB015318
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,3,9-Trimethyluric acid
Description1,3,9-Trimethyluric acid, also known as 1,3,9-trimethylate or 8-oxocaffeine, 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. 1,3,9-Trimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,3,9-Trimethyluric acid has been detected, but not quantified in, coffee and coffee products. This could make 1,3,9-trimethyluric acid a potential biomarker for the consumption of these foods.
CAS Number7464-93-9
Structure
Thumb
Synonyms
SynonymSource
1,3,9-TrimethylateGenerator
1,3,9-Trimethylic acidGenerator
1,3,9-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
7,9-Dihydro-1,3,9-trimethyl-1H-purine-2,6,8(3H)-trioneHMDB
8-OxocaffeineHMDB
1,3,9-trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trionebiospider
1,3,9-Trimethyluric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility29 g/LALOGPS
logP-0.46ALOGPS
logP-0.87ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)7.78ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.96 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.32 m³·mol⁻¹ChemAxon
Polarizability19.76 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H10N4O3
IUPAC name1,3,9-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
InChI IdentifierInChI=1S/C8H10N4O3/c1-10-5-4(9-7(10)14)6(13)12(3)8(15)11(5)2/h1-3H3,(H,9,14)
InChI KeyCWENCZHQIWXCCA-UHFFFAOYSA-N
Isomeric SMILESCN1C(=O)NC2=C1N(C)C(=O)N(C)C2=O
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 45.71%; H 4.80%; N 26.66%; O 22.84%DFC
Melting PointMp 335° dec.DFC
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 KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-2910000000-6282aab8072b7e149b80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-2502fd56810d56eea853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0790000000-8a65f129c8151d98a863JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wb9-3900000000-2c1f0413f2c6b3dc3f13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-30bafcc29f7f8f52e84cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-16f3b19561d03e23d20bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-4900000000-6ad4bacaedfffaa2f502JSpectraViewer
ChemSpider ID73977
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID81972
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36431
CRC / DFC (Dictionary of Food Compounds) IDJZR60-K:JZN50-N
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