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Record Information
Version3.6
Creation Date2006-08-13 18:16:22 UTC
Update Date2016-02-11 01:06:44 UTC
HMDB IDHMDB04400
Secondary Accession NumbersNone
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 KeyInChIKey=POQOTWQIYYNXAT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • Pyrimidone
  • Aminopyrimidine
  • Pyrimidine
  • Primary aromatic amine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Acetamide
  • Vinylogous amide
  • Urea
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
logP-1.1ALOGPS
logP-2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)2.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.87 m3·mol-1ChemAxon
Polarizability18.36 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Caffeine MetabolismSMP00028map00232
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified5.06 +/- 0.13 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
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
NuGOwiki LinkHMDB04400
Metagene LinkHMDB04400
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. [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. [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. [12534641 ]