Showing metabocard for 7-Methylguanosine (BMDB0001107)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:11 UTC
Update Date2020-04-22 15:06:43 UTC
BMDB IDBMDB0001107
Secondary Accession Numbers
  • BMDB01107
Metabolite Identification
Common Name7-Methylguanosine
Description7-Methylguanosine, also known as G, 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. Based on a literature review a significant number of articles have been published on 7-Methylguanosine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GChEBI
m7gChEBI
N(7)-MethylguanosineChEBI
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
N(2)-MethylguanosineMeSH, HMDB
2-MethylguanosineMeSH, HMDB
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-9lambda5-purin-9-ylium
Traditional Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-9lambda5-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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
logP-1.4ALOGPS
logP-6.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.01ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area146.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.38 m³·mol⁻¹ChemAxon
Polarizability28.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001107
DrugBank IDDB03493
Phenol Explorer Compound IDNot Available
FooDB IDFDB022428
KNApSAcK IDC00051958
Chemspider ID393054
KEGG Compound IDNot Available
BioCyc IDCPD0-1041
BiGG IDNot Available
Wikipedia Link7-Methylguanosine
METLIN ID6008
PubChem Compound445404
PDB IDNot Available
ChEBI ID20794
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Protein argonaute-2
General function:
Involved in endoribonuclease activity, cleaving siRNA-p
Specific function:
Required for RNA-mediated gene silencing (RNAi) by the RNA-induced silencing complex (RISC). The 'minimal RISC' appears to include AGO2 bound to a short guide RNA such as a microRNA (miRNA) or short interfering RNA (siRNA). These guide RNAs direct RISC to complementary mRNAs that are targets for RISC-mediated gene silencing. The precise mechanism of gene silencing depends on the degree of complementarity between the miRNA or siRNA and its target. Binding of RISC to a perfectly complementary mRNA generally results in silencing due to endonucleolytic cleavage of the mRNA specifically by AGO2. Binding of RISC to a partially complementary mRNA results in silencing through inhibition of translation, and this is independent of endonuclease activity. May inhibit translation initiation by binding to the 7-methylguanosine cap, thereby preventing the recruitment of the translation initiation factor eIF4-E. May also inhibit translation initiation via interaction with EIF6, which itself binds to the 60S ribosomal subunit and prevents its association with the 40S ribosomal subunit. The inhibition of translational initiation leads to the accumulation of the affected mRNA in cytoplasmic processing bodies (P-bodies), where mRNA degradation may subsequently occur. In some cases RISC-mediated translational repression is also observed for miRNAs that perfectly match the 3' untranslated region (3'-UTR). Can also up-regulate the translation of specific mRNAs under certain growth conditions. Binds to the AU element of the 3'-UTR of the TNF (TNF-alpha) mRNA and up-regulates translation under conditions of serum starvation. Also required for transcriptional gene silencing (TGS), in which short RNAs known as antigene RNAs or agRNAs direct the transcriptional repression of complementary promoter regions.
Gene Name:
AGO2
Uniprot ID:
Q6QME8
Molecular weight:
97388.0