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Showing metabocard for FAPy-adenine (HMDB0004816)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 12:46:15 UTC
Update Date2020-02-26 21:25:14 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
Data?1582752314
MOLSDFPDBSMILESInChI
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
FAPy-adenineChEBI
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
Description 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
  • Hydropyrimidine
  • 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
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

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 Charge1ChemAxon
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
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, Positivesplash10-0ufr-1900000000-45bbdffd7c63dc2ad058Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-4a0fc6b79756178bf145Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-7900000000-5f7889690f5f7e2e158dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01c0-9200000000-6b9e38b9344f72ce9a62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0900000000-f723c3b9131de0382018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-dfe529e454eefc110bb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9200000000-e3877564447431d51b02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0900000000-bfbcfbf97f3ee4f1b946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5900000000-ea9395e164592cd53db7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-917c8ef3e8355522c9beSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 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
Phenol Explorer Compound IDNot Available
FooDB 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 ID27983
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]