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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2023-02-21 17:16:04 UTC
HMDB IDHMDB0002026
Secondary Accession Numbers
  • HMDB02026
Metabolite Identification
Common Name1,9-Dimethyluric acid
Description1,9-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,9-Methyluracil 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. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID:11712316 , 15833286 , 3506820 , 15013152 ).
Structure
Data?1676999764
Synonyms
ValueSource
1,9-DimethylateGenerator
1,9-Dimethylic acidGenerator
1,9-Dimethyl-2,6,8-trihydroxypurineHMDB
7,9-dihydro-1,9-Dimethyl-1H-purine-2,6,8(3H)-trioneHMDB
Chemical FormulaC7H8N4O3
Average Molecular Weight196.1634
Monoisotopic Molecular Weight196.059640142
IUPAC Name1,9-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,9-dimethyl-3,7-dihydropurine-2,6,8-trione
CAS Registry Number55441-62-8
SMILES
CN1C(=O)NC2=C1NC(=O)N(C)C2=O
InChI Identifier
InChI=1S/C7H8N4O3/c1-10-4-3(8-6(10)13)5(12)11(2)7(14)9-4/h1-2H3,(H,8,13)(H,9,14)
InChI KeyUARKDOLETOEBCU-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.4 g/LALOGPS
logP-0.7ALOGPS
logP-1.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.69ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.75 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.42 m³·mol⁻¹ChemAxon
Polarizability17.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.5331661259
DarkChem[M-H]-142.24731661259
DeepCCS[M+H]+134.42230932474
DeepCCS[M-H]-132.02630932474
DeepCCS[M-2H]-167.15930932474
DeepCCS[M+Na]+141.66830932474
AllCCS[M+H]+140.632859911
AllCCS[M+H-H2O]+136.432859911
AllCCS[M+NH4]+144.532859911
AllCCS[M+Na]+145.632859911
AllCCS[M-H]-139.532859911
AllCCS[M+Na-2H]-139.932859911
AllCCS[M+HCOO]-140.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,9-Dimethyluric acidCN1C(=O)NC2=C1NC(=O)N(C)C2=O2599.1Standard polar33892256
1,9-Dimethyluric acidCN1C(=O)NC2=C1NC(=O)N(C)C2=O2123.3Standard non polar33892256
1,9-Dimethyluric acidCN1C(=O)NC2=C1NC(=O)N(C)C2=O2189.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,9-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2C2007.6Semi standard non polar33892256
1,9-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2C2218.5Standard non polar33892256
1,9-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2C2893.3Standard polar33892256
1,9-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C)C1=O1991.1Semi standard non polar33892256
1,9-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C)C1=O2267.1Standard non polar33892256
1,9-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C)C1=O2964.9Standard polar33892256
1,9-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O1977.7Semi standard non polar33892256
1,9-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O2261.0Standard non polar33892256
1,9-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O2475.6Standard polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2201.2Semi standard non polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2427.7Standard non polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2857.0Standard polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2192.2Semi standard non polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2477.5Standard non polar33892256
1,9-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C(N(C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2907.2Standard polar33892256
1,9-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2380.3Semi standard non polar33892256
1,9-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2687.9Standard non polar33892256
1,9-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N(C)C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2585.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,9-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-1900000000-344560c95eceb14839d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,9-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,9-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0002-0900000000-48b45495c7756aeca0362012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4i-9000000000-6ac1f12cc1d0799b789d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-052f-8900000000-76267ac79488a5196b752012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid LC-ESI-QTOF , negative-QTOFsplash10-0002-0900000000-6b32bd91f8955aefa7952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid LC-ESI-QTOF , negative-QTOFsplash10-000j-0900000000-c4bf48dd1b46b66df0502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-4ea54ddfcf5049746dc12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-fa93fd789679e3751d852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Negative-QTOFsplash10-000j-0900000000-c4bf48dd1b46b66df0502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Negative-QTOFsplash10-0002-0900000000-031289426b67101058122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Positive-QTOFsplash10-0002-0900000000-4ea54ddfcf5049746dc12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Positive-QTOFsplash10-0006-0900000000-fa93fd789679e3751d852021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Positive-QTOFsplash10-0002-0900000000-2e7ef88abf7afa19f68b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Positive-QTOFsplash10-0007-0900000000-d232eb99380f28f2b3162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 40V, Positive-QTOFsplash10-0bu0-9400000000-b5d7d6998141471de9e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Negative-QTOFsplash10-0002-1900000000-8a8e243adff570e615732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Negative-QTOFsplash10-0002-1900000000-8e73211b19a684b9b4782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 40V, Negative-QTOFsplash10-0r0u-9500000000-2dfc29a09af72374a79a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Negative-QTOFsplash10-0002-0900000000-8ba3918ee48755b0ba1a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Negative-QTOFsplash10-00kk-0900000000-276366253652ee33ff392021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 40V, Negative-QTOFsplash10-02a9-4900000000-b6e1503979d70e25f5aa2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 10V, Positive-QTOFsplash10-0002-0900000000-0e499ff6f23e328dc54a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 20V, Positive-QTOFsplash10-0002-0900000000-1a330eb0c40452d015cc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,9-Dimethyluric acid 40V, Positive-QTOFsplash10-0a4i-9300000000-4c20ed670bb864c728702021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022804
KNApSAcK IDNot Available
Chemspider ID97753
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108712
PDB IDNot Available
ChEBI ID173963
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBiltz, Heinrich; Pardon, Heinz. Action of chlorine upon methylated and acetylated uric acids. Ann. (1935), 515 201-52.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
  2. Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
  3. Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
  4. Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]