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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:26 UTC
HMDB IDHMDB01107
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-Methylguanosine
Description7-methylguanosine 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.DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. When chemical bonds to DNA, the DNA becomes damaged and proper and complete replication cannot occur to make the normal intended cell. A DNA adduct is an abnormal piece of DNA covalently-bonded to a cancer-causing chemical. This has shown to be the start of a cancerous cell, or carcinogenesis. DNA adducts in scientific experiments are used as bio-markers and as such are themselves measured to reflect quantitatively, for comparison, the amount of cancer in the subject. 7-Methylguanosine is a substrate for purine-nucleoside phosphorylase and Eukaryotic translation initiation factor 4E. (PMID: 3506820 , 17044778 , 17264127 , 16799933 ).
Structure
Thumb
Synonyms
  1. 2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-D-ribofuranosyl-1H-Purinium
  2. 2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-delta-ribofuranosyl-1H-Purinium
Chemical FormulaC11H16N5O5
Average Molecular Weight298.2752
Monoisotopic Molecular Weight298.115143647
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-1,3,7,9$l^{5}-purin-9-ylium
Traditional IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-1,3,7,9$l^{5}-purin-9-ylium
CAS Registry Number20244-86-4
SMILES
CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1
InChI KeyOGHAROSJZRTIOK-KQYNXXCUSA-O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleosides and Analogues
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • methylguanosine(ChEBI)
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Nucleosides and Analogues
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein component
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.61 g/LALOGPS
logP-1.4ALOGPS
logP-6.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.16ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area146.21ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.38ChemAxon
Polarizability28.49ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB022428
KNApSAcK IDNot Available
Chemspider ID393054
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01107
Metagene LinkHMDB01107
METLIN ID6008
PubChem Compound445404
PDB IDMG7
ChEBI ID20794
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Reynaud C, Bruno C, Boullanger P, Grange J, Barbesti S, Niveleau A: Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. Cancer Lett. 1992 Jan 31;61(3):255-62. Pubmed: 1739950
  2. Topp H, Sander G, Heller-Schoch G, Schoch G: Determination of 7-methylguanine, N2,N2-dimethylguanosine, and pseudouridine in ultrafiltrated serum of healthy adults by high-performance liquid chromatography. Anal Biochem. 1987 Feb 15;161(1):49-56. Pubmed: 2437827
  3. Tebib JG, Reynaud C, Cedoz JP, Letroublon MC, Niveleau A: Relationship between urinary excretion of modified nucleosides and rheumatoid arthritis process. Br J Rheumatol. 1997 Sep;36(9):990-5. Pubmed: 9376997
  4. 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. Pubmed: 3506820
  5. Cho SH, Jung BH, Lee SH, Lee WY, Kong G, Chung BC: Direct determination of nucleosides in the urine of patients with breast cancer using column-switching liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2006 Nov;20(11):1229-36. Pubmed: 16799933
  6. Yang TH, Hu ML: Intracellular levels of S-adenosylhomocysteine but not homocysteine are highly correlated to the expression of nm23-H1 and the level of 5-methyldeoxycytidine in human hepatoma cells with different invasion activities. Nutr Cancer. 2006;55(2):224-31. Pubmed: 17044778
  7. Liu Z, Liu S, Xie Z, Blum W, Perrotti D, Paschka P, Klisovic R, Byrd J, Chan KK, Marcucci G: Characterization of in vitro and in vivo hypomethylating effects of decitabine in acute myeloid leukemia by a rapid, specific and sensitive LC-MS/MS method. Nucleic Acids Res. 2007;35(5):e31. Epub 2007 Jan 30. Pubmed: 17264127