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Showing Compound 1,3,7-Trimethyluric acid (FDB022854)

Record Information
Version1.0
Creation date2011-09-21 00:20:36 UTC
Update date2020-09-17 15:41:40 UTC
Primary IDFDB022854
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,3,7-Trimethyluric acid
Description1,3,7-Trimethyluric acid, also known as 8-oxy-caffeine or 1,3,7-trimethylate, 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. 1,3,7-Trimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,3,7-Trimethyluric acid exists in all living organisms, ranging from bacteria to humans. 1,3,7-trimethyluric acid can be biosynthesized from caffeine; which is catalyzed by the enzymes cytochrome P450 1A2, cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C9, and cytochrome P450 2E1. In humans, 1,3,7-trimethyluric acid is involved in caffeine metabolism. Outside of the human body, 1,3,7-Trimethyluric acid has been detected, but not quantified in, several different foods, such as rubus (blackberry, raspberry), passion fruits, mountain yams, wasabis, and pigeon pea. This could make 1,3,7-trimethyluric acid a potential biomarker for the consumption of these foods. An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8, and the nitrogens at positions 1, 3, and 7 are substituted by methyl groups.
CAS Number5415-44-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,3,7-Trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneChEBI
1,3,7-TrimethylurateChEBI
7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trioneChEBI
8-OxocaffeineChEBI
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
8-hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dionehmdb
8-oxy-caffeinehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Foods
  • Cocoa and cocoa products

    • Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MS1,3,7-Trimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1900000000-7ceff209b1b0d4f92cf0Spectrum
    Predicted GC-MS1,3,7-Trimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4c2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636b2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd82012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0900000000-5316637dfdcce19f087a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0imj-3930000000-0593f0aaec496efc76962021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000f-9500000000-fb28fd8903d55811b0a12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-0910000000-eca560d36d14fb72dfe92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-6d4b9f5e8e42f3040e5e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000l-7900000000-2ba0d4f876fceab5182f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000f-9700000000-a42f3584a2bad7add22d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052o-1920000000-53b778bbd3181f2ed83a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000l-3900000000-4305cd286c077e5210792021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0690000000-62dc7eb029289b61c3b12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000f-0900000000-3eb9fdcfd2e67d0f4e2c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-f438ad2b70b2e97356432021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-42add8be62bbafed200c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2930000000-2855ca36942d5e8f069e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9200000000-708fd95bbe618c2ace7d2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfb2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f5242015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a92015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f932015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c772015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03f2015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID71754
    ChEMBL IDCHEMBL1767
    KEGG Compound IDC16361
    Pubchem Compound ID79437
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB02123
    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
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference