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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:04 UTC
HMDB IDHMDB0002032
Secondary Accession Numbers
  • HMDB0011613
  • HMDB02032
  • HMDB11613
Metabolite Identification
Common Name8-Hydroxyguanine
DescriptionFormation of 8-hydroxyguanine (8-OHG), a mutagenic base which is a marker for OH-mediated DNA damage, requires peroxidase and halides and occurs in the presence of transition metal chelators (DTPA +/- desferrioxamine), and is inhibited by catalase, superoxide dismutase (SOD), and scavengers of hypohalous acids. (PMID 10820020 ). 8-Hydroxyguanine is an oxidative stress marker for diagnosis of Alzheimer's disease (AD). (PMID 15977989 ).
Structure
Data?1676999764
Synonyms
ValueSource
8-OxoguanineChEBI
1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dioneHMDB
2-amino-6,8-DihydroxypurineHMDB, MeSH
2-amino-7,9-dihydro-1H-Purine-6,8-dioneHMDB
2-amino-Purine-6,8-diolHMDB
2-Aminopurine-6,8-diolHMDB
7,8-dihydro-8-OxoguanineHMDB
oxo-8-GuaMeSH, HMDB
8-oxo-7,8-DihydroguanineMeSH, HMDB
8-HydroxyguanineChEBI
Chemical FormulaC5H5N5O2
Average Molecular Weight167.1255
Monoisotopic Molecular Weight167.044324429
IUPAC Name2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional Name8-hydroxyguanine
CAS Registry Number5614-64-2
SMILES
NC1=NC2=C(NC(=O)N2)C(=O)N1
InChI Identifier
InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
InChI KeyCLGFIVUFZRGQRP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.94 g/LALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)3.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.81 m³·mol⁻¹ChemAxon
Polarizability14.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.17131661259
DarkChem[M-H]-133.55631661259
DeepCCS[M+H]+134.51230932474
DeepCCS[M-H]-131.52430932474
DeepCCS[M-2H]-168.10930932474
DeepCCS[M+Na]+143.59330932474
AllCCS[M+H]+135.632859911
AllCCS[M+H-H2O]+131.132859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-130.532859911
AllCCS[M+Na-2H]-131.132859911
AllCCS[M+HCOO]-131.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HydroxyguanineNC1=NC2=C(NC(=O)N2)C(=O)N13130.2Standard polar33892256
8-HydroxyguanineNC1=NC2=C(NC(=O)N2)C(=O)N12084.8Standard non polar33892256
8-HydroxyguanineNC1=NC2=C(NC(=O)N2)C(=O)N12319.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxyguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]12168.6Semi standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]12224.3Standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]13547.1Standard polar33892256
8-Hydroxyguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N22103.0Semi standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N22233.6Standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N23306.3Standard polar33892256
8-Hydroxyguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O2131.0Semi standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O2245.1Standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O3381.6Standard polar33892256
8-Hydroxyguanine,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O2192.5Semi standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O2212.3Standard non polar33892256
8-Hydroxyguanine,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O3461.5Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C2062.0Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C2280.2Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C3205.3Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]12057.9Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]12381.4Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]13203.2Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]22105.7Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]22205.3Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]23114.5Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C2128.3Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C2320.9Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C3169.8Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #5C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C1N=C(N)[NH]C2=O2142.6Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #5C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C1N=C(N)[NH]C2=O2266.7Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #5C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C1N=C(N)[NH]C2=O3025.0Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #6C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]22166.5Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #6C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]22255.9Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #6C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]23112.7Standard polar33892256
8-Hydroxyguanine,2TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C)C1=O2117.7Semi standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C)C1=O2308.8Standard non polar33892256
8-Hydroxyguanine,2TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C)C1=O3167.0Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]1)[Si](C)(C)C2041.2Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]1)[Si](C)(C)C2317.1Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)[NH]1)[Si](C)(C)C2790.0Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2081.9Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2221.6Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2643.5Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #3C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2123.7Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #3C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2361.6Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #3C[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2795.9Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2039.5Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2223.9Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2855.2Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #5C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C2082.0Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #5C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C2345.4Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #5C[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C2824.0Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]22131.1Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]22252.3Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]22781.1Standard polar33892256
8-Hydroxyguanine,3TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2132.9Semi standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2242.7Standard non polar33892256
8-Hydroxyguanine,3TMS,isomer #7C[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2956.6Standard polar33892256
8-Hydroxyguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2145.2Semi standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2246.6Standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2443.8Standard polar33892256
8-Hydroxyguanine,4TMS,isomer #2C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2185.4Semi standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #2C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2368.3Standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #2C[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C)C(=O)N1[Si](C)(C)C)[Si](C)(C)C2495.4Standard polar33892256
8-Hydroxyguanine,4TMS,isomer #3C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2211.7Semi standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #3C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2314.9Standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #3C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)[NH]2)[Si](C)(C)C2424.1Standard polar33892256
8-Hydroxyguanine,4TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2171.5Semi standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2276.3Standard non polar33892256
8-Hydroxyguanine,4TMS,isomer #4C[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2571.8Standard polar33892256
8-Hydroxyguanine,5TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2297.5Semi standard non polar33892256
8-Hydroxyguanine,5TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2372.0Standard non polar33892256
8-Hydroxyguanine,5TMS,isomer #1C[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2300.6Standard polar33892256
8-Hydroxyguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]12364.1Semi standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]12438.5Standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]13520.2Standard polar33892256
8-Hydroxyguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N22325.1Semi standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N22410.9Standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1C(=O)[NH]C(N)=N23301.0Standard polar33892256
8-Hydroxyguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O2321.4Semi standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O2475.6Standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C1N=C(N)[NH]C2=O3357.3Standard polar33892256
8-Hydroxyguanine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O2387.7Semi standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O2446.6Standard non polar33892256
8-Hydroxyguanine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)[NH]2)C1=O3427.6Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C(C)(C)C2450.1Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C(C)(C)C2700.1Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)[NH]1)[Si](C)(C)C(C)(C)C3129.5Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]12465.6Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]12716.5Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]13131.6Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22485.8Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22588.6Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]23079.7Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C2554.3Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C2758.5Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C3102.6Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1N=C(N)[NH]C2=O2464.9Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1N=C(N)[NH]C2=O2652.6Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1N=C(N)[NH]C2=O3024.3Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22549.6Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22643.9Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]23082.3Standard polar33892256
8-Hydroxyguanine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O2537.2Semi standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O2695.1Standard non polar33892256
8-Hydroxyguanine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O3113.1Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]1)[Si](C)(C)C(C)(C)C2580.3Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]1)[Si](C)(C)C(C)(C)C2914.8Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)[NH]1)[Si](C)(C)C(C)(C)C2880.6Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C2599.2Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C2855.8Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C2805.0Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2644.7Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2985.1Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)[NH]2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2886.8Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2605.1Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2825.5Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2959.6Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2689.8Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2926.0Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2909.2Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22705.9Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22867.0Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]22894.9Standard polar33892256
8-Hydroxyguanine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2699.3Semi standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2865.4Standard non polar33892256
8-Hydroxyguanine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3041.3Standard polar33892256
8-Hydroxyguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2785.6Semi standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3067.2Standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)[NH]1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2795.9Standard polar33892256
8-Hydroxyguanine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2864.8Semi standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3168.4Standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.6Standard polar33892256
8-Hydroxyguanine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C2880.1Semi standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C3111.9Standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)[Si](C)(C)C(C)(C)C2781.6Standard polar33892256
8-Hydroxyguanine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2903.5Semi standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3077.1Standard non polar33892256
8-Hydroxyguanine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2882.5Standard polar33892256
8-Hydroxyguanine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3123.9Semi standard non polar33892256
8-Hydroxyguanine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3293.6Standard non polar33892256
8-Hydroxyguanine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC2=C(C(=O)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2791.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyguanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3900000000-58549cee828db799d7b52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 10V, Positive-QTOFsplash10-014i-0900000000-6a4117b10e55300957072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 20V, Positive-QTOFsplash10-014i-0900000000-89fdc38268686eaba66a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 40V, Positive-QTOFsplash10-107l-9600000000-7c79695abe7a158747252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 10V, Negative-QTOFsplash10-014i-0900000000-ac22897692beb4981ede2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 20V, Negative-QTOFsplash10-014i-2900000000-f3b3767a022d716580d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 40V, Negative-QTOFsplash10-0006-9100000000-9a8d26eff2e742411cb22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 10V, Negative-QTOFsplash10-014i-0900000000-d3890f3472d103400e662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 20V, Negative-QTOFsplash10-00ri-1900000000-59a4be35534659234b6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 40V, Negative-QTOFsplash10-0006-9100000000-7d9830f9bdf455a842832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 10V, Positive-QTOFsplash10-014i-0900000000-2907e7cb009d3747cf212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 20V, Positive-QTOFsplash10-014i-0900000000-5795d2965bc15c5daf002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyguanine 40V, Positive-QTOFsplash10-00us-9200000000-fd1acc84bba1739821db2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0001 +/- 0.00015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.68 (0.49-0.87) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.005 +/- 0.0007 uMAdult (>18 years old)BothDiabetes details
Cerebrospinal Fluid (CSF)Detected and Quantified0.19 (0.15-0.23) uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Shin CS, Moon BS, Park KS, Kim SY, Park SJ, Chung MH, Lee HK: Serum 8-hydroxy-guanine levels are increased in diabetic patients. Diabetes Care. 2001 Apr;24(4):733-7. [PubMed:11315839 ]
Alzheimer's disease
  1. Lovell MA, Markesbery WR: Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Arch Neurol. 2001 Mar;58(3):392-6. [PubMed:11255442 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022809
KNApSAcK IDNot Available
Chemspider ID58661
KEGG Compound IDC20155
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Oxoguanine
METLIN IDNot Available
PubChem Compound65154
PDB IDNot Available
ChEBI ID52617
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000370
Good Scents IDNot Available
References
Synthesis ReferenceUsacheva A M; Chernikov A V; Bruskov V I Formation of 8-hydroxyguanine upon damage of guanine nucleotides by gamma radiation. Molekuliarnaia biologiia (1995), 29(2), 446-51.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lovell MA, Markesbery WR: Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Arch Neurol. 2001 Mar;58(3):392-6. [PubMed:11255442 ]
  2. Shen Z, Wu W, Hazen SL: Activated leukocytes oxidatively damage DNA, RNA, and the nucleotide pool through halide-dependent formation of hydroxyl radical. Biochemistry. 2000 May 9;39(18):5474-82. [PubMed:10820020 ]
  3. Flirski M, Sobow T: Biochemical markers and risk factors of Alzheimer's disease. Curr Alzheimer Res. 2005 Jan;2(1):47-64. [PubMed:15977989 ]