Human Metabolome Database Version 3.5

Showing metabocard for 7-Methylguanosine (HMDB01107)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:26 -0600
HMDB ID HMDB01107
Secondary Accession Numbers None
Metabolite Identification
Common Name 7-Methylguanosine
Description 7-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 Link_out, 17044778 Link_out, 17264127 Link_out, 16799933 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C11H16N5O5
Average Molecular Weight 298.2752
Monoisotopic Molecular Weight 298.115143647
IUPAC Name 2-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$l^{5}-purin-9-ylium
Traditional IUPAC Name 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-1,3,7,9$l^{5}-purin-9-ylium
CAS Registry Number 20244-86-4
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 Key OGHAROSJZRTIOK-KQYNXXCUSA-O
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class N/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 Parent Purine Nucleosides and Analogues
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein component
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 155 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.61 g/L ALOGPS
LogP -1.43 ALOGPS
LogP -6.2 ChemAxon
LogS -1.77 ALOGPS
pKa (strongest acidic) 8.16 ChemAxon
pKa (strongest basic) -2.1 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 146.21 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 69.38 ChemAxon
Polarizability 28.49 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022428
KNApSAcK ID Not Available
Chemspider ID 393054 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01107 Link_out
Metagene Link HMDB01107 Link_out
METLIN ID 6008 Link_out
PubChem Compound 445404 Link_out
PDB ID MG7 Link_out
ChEBI ID 20794 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out