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Showing metabocard for 5-Acetylamino-6-formylamino-3-methyluracil (HMDB0011105)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-10-16 22:24:20 UTC
Update Date2020-02-26 21:34:28 UTC
HMDB IDHMDB0011105
Secondary Accession Numbers
  • HMDB11105
Metabolite Identification
Common Name5-Acetylamino-6-formylamino-3-methyluracil
Description5-Acetylamino-6-formylamino-3-methyluracil, also known as AFMU, belongs to the class of organic compounds 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. 5-Acetylamino-6-formylamino-3-methyluracil is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-acetylamino-6-formylamino-3-methyluracil can be biosynthesized from paraxanthine and acetyl-CoA; which is catalyzed by the enzyme arylamine N-acetyltransferase 2. In humans, 5-acetylamino-6-formylamino-3-methyluracil is involved in caffeine metabolism.
Structure
Data?1582752868
MOLSDFPDBSMILESInChI
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
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
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

Source:

Biological location:

Process

Naturally occurring process:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02aj-0920000000-16da22a4333f0fee7510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0920000000-d1d7f82a38e95c7a5d71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-c5b7ff32f7d723272262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vi-9800000000-9ba04a2c080cb26d9580Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2930000000-71c3ffa165db7a3dcefcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9510000000-29be496cfae1206b4acaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9200000000-495d6d6c6250fa932789Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified5.11 +/- 0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027888
KNApSAcK IDNot Available
Chemspider ID97287
KEGG Compound IDC16365
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108214
PDB IDNot Available
ChEBI ID32643
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Arylamine N-acetyltransferase 1
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
Enzyme Details
2. Arylamine N-acetyltransferase 2
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
Enzyme Details
3. Arylamine N-acetyltransferase 2
General function:
Involved in acetyltransferase activity
Specific function:
Not Available
Gene Name:
NAT2
Uniprot ID:
A4Z6T7
Molecular weight:
33570.2