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Record Information
Version3.6
Creation Date2006-08-24 12:46:15 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04816
Secondary Accession NumbersNone
Metabolite Identification
Common NameFAPy-adenine
DescriptionFapy-adenine is an oxidized DNA base. Oxidized nucleosides are biochemical markers for tumors, aging, and neurodegenerative diseases. (PMID 15116424 ). Oxidative stress damage to DNA bases may contribute to neuronal loss in Alzheimer's disease (AD). Increased levels were observed in parietal, temporal, occipital, and frontal lobe, superior temporal gyrus, and hippocampus areas of the brain in patients with AD. (PMID 9109533 ).
Structure
Thumb
Synonyms
ValueSource
4,6-diamino-5-(formylamino)PyrimidineChEBI
4,6-diamino-5-N-FormamidopyrimidineChEBI
4,6-diamino-5-PyrimidinylformamideChEBI
FAPYChEBI
FAPy-adenineChEBI
FapyadeChEBI
4,6-diamino-5-FormamidopyrimidineHMDB
N-(4,6-diamino-5-Pyrimidinyl)-formamideHMDB
N-(4,6-diamino-5-Pyrimidinyl)formamideHMDB
Chemical FormulaC5H7N5O
Average Molecular Weight153.142
Monoisotopic Molecular Weight153.065059871
IUPAC NameN-(4,6-diaminopyrimidin-5-yl)formamide
Traditional NameN-(4,6-diaminopyrimidin-5-yl)formamide
CAS Registry Number5122-36-1
SMILES
NC1=NC=NC(N)=C1NC=O
InChI Identifier
InChI=1S/C5H7N5O/c6-4-3(10-2-11)5(7)9-1-8-4/h1-2H,(H,10,11)(H4,6,7,8,9)
InChI KeyInChIKey=MVYUVUOSXNYQLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminopyrimidines and derivatives. These are organic compounds containing an amino 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 ParentAminopyrimidines and derivatives
Alternative Parents
Substituents
  • Aminopyrimidine
  • Imidolactam
  • Primary aromatic amine
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point224 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.67 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.93ChemAxon
pKa (Strongest Basic)6.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.92 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.12 m3·mol-1ChemAxon
Polarizability13.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-4a0fc6b79756178bf145View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-7900000000-5f7889690f5f7e2e158dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01c0-9200000000-6b9e38b9344f72ce9a62View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.31 (0.22-0.4) 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 IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023426
KNApSAcK IDNot Available
Chemspider ID102870
KEGG Compound IDC06502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04816
Metagene LinkHMDB04816
METLIN ID7080
PubChem Compound114926
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHaley, C. A. C.; Maitland, P. Organic reactions in aqueous solution at room temperature. I. The influence of pH on condensations involving the linking of carbon to nitrogen and of carbon to carbon. Journal of the Chemical Society (1951), 3155-74.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [15116424 ]
  2. Lyras L, Cairns NJ, Jenner A, Jenner P, Halliwell B: An assessment of oxidative damage to proteins, lipids, and DNA in brain from patients with Alzheimer's disease. J Neurochem. 1997 May;68(5):2061-9. [9109533 ]