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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:34:11 UTC
Update Date2019-07-23 06:21:14 UTC
HMDB IDHMDB0036431
Secondary Accession Numbers
  • HMDB36431
Metabolite Identification
Common Name1,3,9-Trimethyluric acid
Description1,3,9-Trimethyluric acid is found in coffee and coffee products. 1,3,9-Trimethyluric acid is present in roasted coffee beans and instant coffee, but not green coffee beans.
Structure
Data?1563862874
Synonyms
ValueSource
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
Chemical FormulaC8H10N4O3
Average Molecular Weight210.19
Monoisotopic Molecular Weight210.075290206
IUPAC Name1,3,9-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,3,9-trimethyl-7H-purine-2,6,8-trione
CAS Registry Number7464-93-9
SMILES
CN1C(=O)NC2=C1N(C)C(=O)N(C)C2=O
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point335 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-2910000000-6282aab8072b7e149b80JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-2502fd56810d56eea853JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0790000000-8a65f129c8151d98a863JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wb9-3900000000-2c1f0413f2c6b3dc3f13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-30bafcc29f7f8f52e84cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-16f3b19561d03e23d20bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-4900000000-6ad4bacaedfffaa2f502JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015318
KNApSAcK IDNot Available
Chemspider ID73977
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound81972
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .