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-AMMUMeSH
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Acetylamino-6-amino-3-methyluracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-2900000000-2d2fce0f3b41d6ee5ed5Spectrum
Predicted GC-MS5-Acetylamino-6-amino-3-methyluracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Acetylamino-6-amino-3-methyluracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-006y-9200000000-bc1b2146eec01e767a75Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002e-4900000000-1d19aed0d341cc4d9210Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-c3d8379066da662149e1Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-007o-9400000000-ea9d970e92f2c9069413Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e51004c20cbfc1d4f944Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0gx1-0920000000-1c3930bbd99354dc64bcSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0cdi-5900000000-049dcbea7599c459514bSpectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0900000000-9f886b28f5f0dc3c490dSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-006y-9000000000-5981916c239c2705d949Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c0932a165f81ee34af30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0900000000-6d6bb4381c239bd1e83fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-72b405e1279632249e5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-b93fa98027956aaaa8f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-1c50114eb8bce95366bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9800000000-91e073b0e556bcd2bd2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-9000000000-1cc734e6cf6743ce30a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-5e285a4ce72c0d3495bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-3900000000-5e5f9a546b5f48946784Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-27fd0995b1c229e56123Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-ca06f4616042dc126edcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0900000000-5d50721d3d88998cf657Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-3452e3a490e46f193900Spectrum
NMRNot Available
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