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Record Information
Version4.0
Creation Date2008-10-16 22:22:16 UTC
Update Date2017-09-27 08:26:25 UTC
HMDB IDHMDB0011103
Secondary Accession Numbers
  • HMDB11103
Metabolite Identification
Common Name1,7-Dimethyluric acid
Description1,7 dimethyluric acid is the major urinary caffeine metabolites that is produced in the human body. 1,7 dimethyluric acid is formed during metabolism of caffeine and the process is catalyzed primarily by CYP2A6. (PMID: 18715882 ).
Structure
Thumb
Synonyms
ValueSource
17-Dimethyluric acidChEMBL
17-DimethylateGenerator
17-Dimethylic acidGenerator
1,7-DimethylateGenerator
1,7-Dimethylic acidGenerator
Chemical FormulaC7H8N4O3
Average Molecular Weight196.1634
Monoisotopic Molecular Weight196.059640142
IUPAC Name1,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,7-dimethyluric acid
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2
InChI Identifier
InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)9-7(14)11(2)5(3)12/h1-2H3,(H,8,13)(H,9,14)
InChI KeyNOFNCLGCUJJPKU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.49 g/LALOGPS
logP-0.81ALOGPS
logP-1.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.16ChemAxon
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
Polarizability17.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Caffeine MetabolismPw000015Pw000015 greyscalePw000015 simpleMap00232
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified3.0 (2.38 - 6.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected and Quantified20.0 (5.7-32.0) umol/mmol creatinineAdult (>18 years old)Both
    Asthma
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    Associated Disorders and Diseases
    Disease References
    Asthma
    1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00611
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB027886
    KNApSAcK IDNot Available
    Chemspider ID82720
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound91611
    PDB IDNot Available
    ChEBI ID149713
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Sinues B, Fanlo A, Mayayo E, Carcas C, Vicente J, Arenaz I, Cebollada A: CYP2A6 activity in a healthy Spanish population: effect of age, sex, smoking, and oral contraceptives. Hum Exp Toxicol. 2008 May;27(5):367-72. doi: 10.1177/0960327107082224. [PubMed:18715882 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
    Gene Name:
    XDH
    Uniprot ID:
    P47989
    Molecular weight:
    146422.99
    Reactions
    Paraxanthine + Oxygen + Water → 1,7-Dimethyluric acid + Hydrogen peroxidedetails
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
    Gene Name:
    CYP1A2
    Uniprot ID:
    P05177
    Molecular weight:
    58406.915