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Record Information
Version4.0
Creation Date2008-10-16 22:24:20 UTC
Update Date2017-09-27 08:26:25 UTC
HMDB IDHMDB0011105
Secondary Accession Numbers
  • HMDB11105
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.82 m³·mol⁻¹ChemAxon
Polarizability20.46 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0920000000-d1d7f82a38e95c7a5d71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-c5b7ff32f7d723272262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vi-9800000000-9ba04a2c080cb26d9580View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2930000000-71c3ffa165db7a3dcefcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9510000000-29be496cfae1206b4acaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9200000000-495d6d6c6250fa932789View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Caffeine MetabolismPw000015Pw000015 greyscalePw000015 simpleMap00232
Displaying 1 entry
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
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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 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
    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