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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2008-10-16 22:26:25 UTC
Update Date2020-11-09 23:18:09 UTC
HMDB IDHMDB0011107
Secondary Accession Numbers
  • HMDB11107
Metabolite Identification
Common Name7-Methyluric acid
Description7-Methyluric acid, also known as 7-methylate, 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. 7-Methyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-Methyluric acid exists in all living organisms, ranging from bacteria to humans. 7-methyluric acid can be biosynthesized from 7-methylxanthine through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, 7-methyluric acid is involved in caffeine metabolism.
Structure
Data?1582752868
Synonyms
ValueSource
7-MethylateGenerator
7-Methylic acidGenerator
Chemical FormulaC6H6N4O3
Average Molecular Weight182.1368
Monoisotopic Molecular Weight182.043990078
IUPAC Name7-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name7-methyluric acid
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC2=C1C(=O)NC(=O)N2
InChI Identifier
InChI=1S/C6H6N4O3/c1-10-2-3(8-6(10)13)7-5(12)9-4(2)11/h1H3,(H3,7,8,9,11,12,13)
InChI KeyYHNNPKUFPWLTOP-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 Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

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 Solubility3.71 g/LALOGPS
logP-1ALOGPS
logP-1.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.37ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability15.65 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, Positivesplash10-03ei-1900000000-48944d897b1adbf7ce06Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-001i-0900000000-d047affd76adf79850f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-001i-0900000000-586897d99a4bf96f59e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-001i-0900000000-76edc65ffad189950defSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-001i-0900000000-98bd5bea3d7112e121f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-015c-0900000000-9bc9bace27b6ee9a6492Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-3900000000-0f68eaedf01ce0b10f9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9600000000-44337706f27a0c5257a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9100000000-5daafdc771ce214d9f0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-014i-9000000000-d2d2560858af2ff10256Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-014i-9000000000-af480b14991f0c34f8c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-014l-0900000000-7ad68dcc2845f0521934Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-014i-9000000000-f647da344adbdf7bfb1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-03di-0900000000-31bc5353954a5354da02Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-000i-0900000000-e15d4534ccde7995ef2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-03di-0900000000-8cd35e2b2191f4fb94a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-1900000000-0ea800756f4ab5ea3d25Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0006-4900000000-eb83967fc3d3b0d6d8f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014l-9600000000-f093dd738be634d15c18Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014i-9200000000-4325df2e79ca823ab375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-dc350a0d473282f926d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-1900000000-a13ac64bd9ab51761cddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9400000000-81688eb86cc318dfd7bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-cf50c6b34fdb182cc93cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1900000000-42d1e6a7e4e45ebdf17fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-7a39d0c29427d4f8cf7fSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027890
KNApSAcK IDNot Available
Chemspider ID62375
KEGG Compound IDC16355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69160
PDB IDNot Available
ChEBI ID149744
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
7-Methylxanthine + Oxygen + Water → 7-Methyluric acid + Hydrogen peroxidedetails