Back to Compounds

7-Methylguanosine (PC000244)

Record Information
Version1.0
Creation date2015-10-09 22:29:25 UTC
Update date2017-01-19 02:36:17 UTC
FoodComEx IDPC000244
FoodDB RecordFDB022428
Chemical Information
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) [HMDB]
CAS Number20244-86-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-amino-6,9-dihydro-7-methyl-6-oxo-9-beta-D-ribofuranosyl-1H-Puriniumhmdb
2-amino-6,9-dihydro-7-methyl-6-oxo-9-beta-delta-ribofuranosyl-1H-Puriniumhmdb
m7gChEBI
N(7)-MethylguanosineChEBI
Chemical FormulaC11H16N5O5
IUPAC name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9lambda5-purin-9-ylium
InChI IdentifierInChI=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
Isomeric SMILESCN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2
Average Molecular Weight298.2752
Monoisotopic Molecular Weight298.115143647
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Primary alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 6830AD
Cayman Chemical 15988
Toronto Research Chemicals M311835