Record Information
Version1.0
Creation date2011-09-21 00:28:51 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023371
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number19893-78-8
Structure
Thumb
Synonyms
SynonymSource
AAMUKegg
5-AMMUHMDB
5-Ammuhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H10N4O3
IUPAC nameN-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
InChI IdentifierInChI=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
Isomeric SMILESCN1C(=O)NC(N)=C(NC(C)=O)C1=O
Average Molecular Weight198.1793
Monoisotopic Molecular Weight198.075290206
Classification
Description belongs to the class of organic compounds known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassN-arylamides
Direct ParentN-acetylarylamines
Alternative Parents
Substituents
  • N-acetylarylamine
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • 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
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-2900000000-2d2fce0f3b41d6ee5ed5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0900000000-6d6bb4381c239bd1e83fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-72b405e1279632249e5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-b93fa98027956aaaa8f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-1c50114eb8bce95366bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9800000000-91e073b0e556bcd2bd2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-9000000000-1cc734e6cf6743ce30a8JSpectraViewer
ChemSpider ID79659
ChEMBL IDCHEMBL1899490
KEGG Compound IDC16366
Pubchem Compound ID88299
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04400
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Caffeine MetabolismSMP00028 map00232
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference