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Record Information
Version3.6
Creation Date2008-10-16 22:24:20 UTC
Update Date2017-03-02 21:31:34 UTC
HMDB IDHMDB11105
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Acetylamino-6-formylamino-3-methyluracil
Description5-Acetylamino-6-formylamino-3-methyluracil participates in Caffeine metabolism. 5-Acetylamino-6-formylamino-3-methyluracil is converted from paraxanthine via arylamine N-acetyltransferase [EC:2.3.1.5].
Structure
Thumb
Synonyms
ValueSource
AFMUChEBI
Chemical FormulaC8H10N4O4
Average Molecular Weight226.1894
Monoisotopic Molecular Weight226.070204828
IUPAC NameN-(6-formamido-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
Traditional NameAFMU
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC(NC=O)=C(NC(C)=O)C1=O
InChI Identifier
InChI=1S/C8H10N4O4/c1-4(14)10-5-6(9-3-13)11-8(16)12(2)7(5)15/h3H,1-2H3,(H,9,13)(H,10,14)(H,11,16)
InChI KeyRDZNZFGKEVDNPK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentHydroxypyrimidines
Alternative Parents
Substituents
  • Pyrimidone
  • Hydroxypyrimidine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.53 mg/mLALOGPS
logP-0.74ALOGPS
logP-2.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.02ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.82 m3·mol-1ChemAxon
Polarizability20.47 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Caffeine MetabolismSMP00028map00232
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified5.11 +/- 0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00612
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB027888
    KNApSAcK IDNot Available
    Chemspider ID97287
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB11105
    Metagene LinkHMDB11105
    METLIN IDNot Available
    PubChem Compound108214
    PDB IDNot Available
    ChEBI ID32643
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General ReferencesNot Available

    Enzymes

    General function:
    Involved in acetyltransferase activity
    Specific function:
    Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
    Gene Name:
    NAT1
    Uniprot ID:
    P18440
    Molecular weight:
    33898.445
    Reactions
    Paraxanthine → 5-Acetylamino-6-formylamino-3-methyluracildetails
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
    Gene Name:
    NAT2
    Uniprot ID:
    P11245
    Molecular weight:
    33570.245
    Reactions
    Paraxanthine → 5-Acetylamino-6-formylamino-3-methyluracildetails
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6T7
    Molecular weight:
    33570.2