Back to Compounds

Showing Compound 8-Hydroxyadenine (FDB022105)

Record Information
Version1.0
Creation date2011-09-21 00:08:34 UTC
Update date2015-07-21 06:56:58 UTC
Primary IDFDB022105
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-Hydroxyadenine
Description8-hydroxyadenine is an intermediate in the oxidation of adenine to 2,8-dihydroxyadenine by xanthine oxidase (EC 1.1.3.22). A controversy exists as to whether or not this metabolite is a marker of DNA damage. Several papers have reported an artifactual formation of a number of modified bases from intact DNA bases during derivatization of DNA hydrolysates to be analyzed by gas chromatography-mass spectrometry (GC/MS). These reports dealt with 8-hydroxyadenine (8-OH). It needs to be emphasized that the procedures for hydrolysis of DNA and derivatization of DNA hydrolysates used in these papers substantially differed from the established procedures previously described. Furthermore, a large number of relevant papers reporting the levels of these modified bases in DNA of various sources have been ignored. Interestingly, the levels of modified bases reported in the literature were not as high as those reported prior to prepurification. Levels of 8-OH-Ade were quite close to, or even the same as, or smaller than the level reported after prepurification. All these facts raise the question of the validity of the claims about the measurement of these modified DNA bases by GC/MS. Oxidative damage to DNA may play an important role in aging and neurodegenerative diseases such as Alzheimer's disease (AD). Attack on DNA by reactive oxygen species, particularly hydroxyl radicals, can lead to strand breaks, DNA-DNA and DNA-protein cross-linking, sister chromatid exchange and translocation, and formation of at least 20 oxidized base adducts. Modification of DNA bases can lead to mutation and altered protein synthesis. In late-stage AD brain, several studies have shown an elevation of the base adducts 8-hydroxyadenine (8-OHA). Several studies have shown a decline in repair of 8-OHG in AD. Most recently studies have shown elevated 8-OHA in nuclear and mitochondrial DNA in mild cognitive impairment, the earliest detectable form of AD, suggesting that oxidative damage to DNA is an early event in AD and not a secondary phenomenon. (PMID: 10098459, 17034348) [HMDB]
CAS Number21149-26-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
logP-0.82ALOGPS
logP-0.19ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)5.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.71 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.67 m³·mol⁻¹ChemAxon
Polarizability13.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H5N5O
IUPAC name6-amino-7H-purin-8-ol
InChI IdentifierInChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)
InChI KeyRGKBRPAAQSHTED-UHFFFAOYSA-N
Isomeric SMILESNC1=NC=NC2=C1NC(O)=N2
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
Classification
Description Belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinones
Alternative Parents
Substituents
  • 6-aminopurine
  • Purinone
  • Aminopyrimidine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8-Hydroxyadenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zmi-2900000000-15799f7dfde6b61d5e9dSpectrum
Predicted GC-MS8-Hydroxyadenine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kmi-5930000000-e3d510cf39e85c0d6c20Spectrum
Predicted GC-MS8-Hydroxyadenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Hydroxyadenine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Hydroxyadenine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Hydroxyadenine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Hydroxyadenine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Hydroxyadenine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-d209f35bcb47000991e22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ccfafe3d723f793a566c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9500000000-8441670cd85efff4fc682017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-7396c5f39ca266e16ca22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-fcac70e143de08e16c172017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c317d7036a3bfb98fedb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-361a2474138028086bb32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-50d8e77d9b1fbd7cf4b12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-7900000000-40365895919344706a262021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-062eb4a75a9800bdbe072021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ul0-0900000000-6b703dbbb8530abc96532021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9200000000-5a08d4210b257200ae712021-09-24View Spectrum
NMRNot Available
ChemSpider ID4511108
ChEMBL IDCHEMBL150192
KEGG Compound IDNot Available
Pubchem Compound ID5355054
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00542
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference