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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-10-16 22:22:16 UTC
Update Date2020-11-09 23:18:07 UTC
HMDB IDHMDB0011103
Secondary Accession Numbers
  • HMDB11103
Metabolite Identification
Common Name1,7-Dimethyluric acid
Description1,7-Dimethyluric acid, also known as 1,7-dimethylate, 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. 1,7-Dimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,7-Dimethyluric acid exists in all living organisms, ranging from bacteria to humans. 1,7-dimethyluric acid can be biosynthesized from paraxanthine; which is mediated by the enzymes cytochrome P450 1A2 and cytochrome P450 2A6. 1,7-Dimethyluric acid is formed during caffeine metabolism and the process is catalyzed primarily by CYP2A6 (PMID: 18715882 ). 1,7 dimethyluric acid is formed during metabolism of caffeine and the process is catalyzed primarily by CYP2A6. In humans, 1,7-dimethyluric acid is involved in caffeine metabolism. 1,7-Dimethyluric acid is the major urinary caffeine metabolite that is produced in the human body. 1,7 dimethyluric acid is the major urinary caffeine metabolites that is produced in the human body.
Structure
Data?1582752867
Synonyms
ValueSource
1,7-DimethylateGenerator
1,7-Dimethylic acidGenerator
1,7-DimethylurateHMDB
7,9-Dihydro-1,7-dimethyl-1H-purine-2,6,8(3H)-trioneHMDB
1,7-Dimethyluric acidHMDB
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 Number33868-03-0
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
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
  • 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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-029l-0900000000-fa683b3e4ecb7c70f206Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-f40482c57d127e32f8e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0007-0900000000-6860551c1745ba41864fSpectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-0900000000-c180cf8aed0912f88a75Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-0900000000-ae0b921d4ce14cd8443dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0900000000-9d422231f3b705d6e815Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-0900000000-440ffa8e3cca49f55cc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0002-0900000000-9191d6a6a1abdd23d811Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0002-0900000000-1b5e888daf17a0165e55Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0005-0900000000-df2cb96313fe3610cc44Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0007-0900000000-6234b012018c1ae4d86eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0006-1900000000-86334014f96303c72304Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0006-6900000000-ca9b5373df8e0ea8fcd3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-01bc-9300000000-7a850dc063e0bf5fd5fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-0006-0900000000-0277172e5e710f4775deSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-03di-6900000000-542cf592e0459e911f5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-00xr-9000000000-db67735b192b87b601b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-000i-0900000000-e0b8225c7958cf0367cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-03di-0900000000-8cd35e2b2191f4fb94a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-004s-3900000000-f3c613d69643e20758ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bd55edf6a44d0c64f3b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-1ba40353172a8d8a0d53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9600000000-9845b1cfa11ec4dcced0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-45f918e65bf50b9c83ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2900000000-683f1d7f14c8b26bd2cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9200000000-9022272eeb07eb313dfdSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.0 (2.38 - 6.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified20.0 (5.7-32.0) umol/mmol creatinineAdult (>18 years old)Both
Asthma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB027886
KNApSAcK IDNot Available
Chemspider ID82720
KEGG Compound IDC16356
BioCyc IDCPD-12483
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91611
PDB IDNot Available
ChEBI ID68449
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000796
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