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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 18:16:22 UTC
Update Date2017-10-23 19:04:11 UTC
HMDB IDHMDB0004400
Secondary Accession Numbers
  • HMDB04400
Metabolite Identification
Common Name5-Acetylamino-6-amino-3-methyluracil
Description5-Acetylamino-6-amino-3-methyluracil (AAMU) is one of caffeine major metabolites. Analysis of caffeine and its metabolites is of interest with respect to caffeine exposure, for kinetic and metabolism studies and for opportunistic in vivo estimation of drug metabolizing enzyme activity in humans and animals. Urinary caffeine metabolite ratios are used in humans to assess the activity of cytochrome P450 1A2 (CYP1A2), xanthine oxidase and N-acetyltransferase 2 (NAT2), which are involved in the activation or detoxification of various xenobiotic compounds, including carcinogens. Investigating the activity of these enzymes is of clinical relevance for assessing intra- and inter-individual differences in NAT2- and CYP1A2-mediated drug metabolism, and for evaluating the risk of developing specific exposure-related diseases. (PMID: 3506820 , 15685651 , 12534641 ).
Structure
Thumb
Synonyms
ValueSource
AAMUKegg
5-AmmuHMDB
Chemical FormulaC7H10N4O3
Average Molecular Weight198.1793
Monoisotopic Molecular Weight198.075290206
IUPAC NameN-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
Traditional NameN-(4-amino-1-methyl-2,6-dioxo-3H-pyrimidin-5-yl)acetamide
CAS Registry Number19893-78-8
SMILES
CN1C(=O)NC(N)=C(NC(C)=O)C1=O
InChI Identifier
InChI=1S/C7H10N4O3/c1-3(12)9-4-5(8)10-7(14)11(2)6(4)13/h8H2,1-2H3,(H,9,12)(H,10,14)
InChI KeyPOQOTWQIYYNXAT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentN-acetylarylamines
Alternative Parents
Substituents
  • N-acetylarylamine
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Primary aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Acetamide
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Urea
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 Solubility2.5 g/LALOGPS
logP-1.1ALOGPS
logP-2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.87 m³·mol⁻¹ChemAxon
Polarizability18.36 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-2900000000-2d2fce0f3b41d6ee5ed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0900000000-6d6bb4381c239bd1e83fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-72b405e1279632249e5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-b93fa98027956aaaa8f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-1c50114eb8bce95366bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9800000000-91e073b0e556bcd2bd2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-9000000000-1cc734e6cf6743ce30a8View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Caffeine MetabolismPw000015Pw000015 greyscalePw000015 simpleMap00232
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.06 +/- 0.13 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023371
KNApSAcK IDNot Available
Chemspider ID79659
KEGG Compound IDC16366
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88299
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
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. Weimann A, Sabroe M, Poulsen HE: Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 2005 Mar;40(3):307-16. [PubMed:15685651 ]
  3. Nyeki A, Buclin T, Biollaz J, Decosterd LA: NAT2 and CYP1A2 phenotyping with caffeine: head-to-head comparison of AFMU vs. AAMU in the urine metabolite ratios. Br J Clin Pharmacol. 2003 Jan;55(1):62-7. [PubMed:12534641 ]