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Record Information
Version3.6
Creation Date2007-04-12 20:56:15 UTC
Update Date2016-02-11 01:07:21 UTC
HMDB IDHMDB06037
Secondary Accession NumbersNone
Metabolite Identification
Common Name8-Hydroxy-7-methylguanine
Description8-Hydroxy-7-methylguanine is a modified nucleoside. 8-Hydroxy-7-methylguanine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls. Human exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair; the N2 position of guanine is one of the major sites for DNA modification by various carcinogens. Measurements of RNA or DNA catabolites in urine can be used as a measure for the metabolism of each of the three major species of RNA. An accumulation of modified ribonucleosides appears in the serum of uremic patients. (PMID: 3506820 , 5961889 , 16527824 , 16061253 , 8043914 , 2428556 , 7159514 , 9607216 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC6H7N5O2
Average Molecular Weight181.1521
Monoisotopic Molecular Weight181.059974493
IUPAC Name2-amino-7-methyl-6,7,8,9-tetrahydro-3H-purine-6,8-dione
Traditional Name2-amino-7-methyl-3,9-dihydropurine-6,8-dione
CAS Registry Number1688-85-3
SMILES
CN1C(=O)NC2=C1C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C6H7N5O2/c1-11-2-3(9-6(11)13)8-5(7)10-4(2)12/h1H3,(H4,7,8,9,10,12,13)
InChI KeyInChIKey=VHPXSVXJBWZORQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. 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 ParentHypoxanthines
Alternative Parents
Substituents
  • Hypoxanthine
  • 6-oxopurine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.03 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.17ChemAxon
pKa (Strongest Basic)0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.82 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.5 m3·mol-1ChemAxon
Polarizability16.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot 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 Quantified0.6 (0.4-0.72) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
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 IDFDB023813
KNApSAcK IDNot Available
Chemspider ID272336
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06037
Metagene LinkHMDB06037
METLIN IDNot Available
PubChem Compound308075
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [9607216 ]
  2. Choi JY, Guengerich FP: Adduct size limits efficient and error-free bypass across bulky N2-guanine DNA lesions by human DNA polymerase eta. J Mol Biol. 2005 Sep 9;352(1):72-90. [16061253 ]
  3. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [3506820 ]
  4. Kanduc D, Sapia G: Origin of 1,7-dimethylguanosine in tRNA chemical and enzymatic methylation. Boll Soc Ital Biol Sper. 1982 Oct 15;58(19):1221-5. [7159514 ]
  5. Litwack MD, Weissmann B: Source of urinary 8-hydroxy-7-methylguanine in man. Biochemistry. 1966 Sep;5(9):3007-12. [5961889 ]
  6. Choi JY, Guengerich FP: Kinetic evidence for inefficient and error-prone bypass across bulky N2-guanine DNA adducts by human DNA polymerase iota. J Biol Chem. 2006 May 5;281(18):12315-24. Epub 2006 Mar 8. [16527824 ]
  7. Porcelli B, Pagani R, Lorenzini L, De Martino A, Catinella S, Traldi P: Different mass spectrometric approaches in the identification of endogenous methylated purine bases in urine extracts. Rapid Commun Mass Spectrom. 1994 Jun;8(6):443-50. [8043914 ]
  8. Sander G, Topp H, Heller-Schoch G, Wieland J, Schoch G: Ribonucleic acid turnover in man:RNA catabolites in urine as measure for the metabolism of each of the three major species of RNA. Clin Sci (Lond). 1986 Oct;71(4):367-74. [2428556 ]