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Record Information
Version4.0
Creation Date2006-08-24 12:46:15 UTC
Update Date2017-09-27 08:24:29 UTC
HMDB IDHMDB0004816
Secondary Accession Numbers
  • HMDB04816
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
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 KeyMVYUVUOSXNYQLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentAminopyrimidines and derivatives
Alternative Parents
Substituents
  • Aminopyrimidine
  • Hydropyrimidine
  • Primary aromatic amine
  • Imidolactam
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.12 m³·mol⁻¹ChemAxon
Polarizability13.85 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
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0900000000-f723c3b9131de0382018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-dfe529e454eefc110bb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9200000000-e3877564447431d51b02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0900000000-bfbcfbf97f3ee4f1b946View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5900000000-ea9395e164592cd53db7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-917c8ef3e8355522c9beView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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
    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. [PubMed: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. [PubMed:9109533 ]