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Record Information
Version3.6
Creation Date2008-10-16 22:24:20 UTC
Update Date2016-02-11 01:20:09 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
5-acetylamino-6-formylamino-3-MethyluracilChEBI
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 KeyInChIKey=RDZNZFGKEVDNPK-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
  • 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
  • Organooxygen compound
  • Carbonyl group
  • 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
SpectraNot 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 QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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