Showing metabocard for 2-Methylguanosine (BMDB0005862)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:19:10 UTC
Update Date2020-05-11 20:41:22 UTC
BMDB IDBMDB0005862
Secondary Accession Numbers
  • BMDB05862
Metabolite Identification
Common Name2-Methylguanosine
Description2-Methylguanosine, also known as M2G, 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 2-Methylguanosine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Methylamino)-9-(beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneChEBI
7-MethylguanosineChEBI
m2gChEBI
2-(Methylamino)-9-(b-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneGenerator
2-(Methylamino)-9-(β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneGenerator
N(2)-MethylguanosineHMDB
N-Methyl guanosineHMDB
N-Methyl-guanosineHMDB
N-MethylguanosineHMDB
2-MethylguanosineChEBI
Chemical FormulaC11H15N5O5
Average Molecular Weight297.2673
Monoisotopic Molecular Weight297.107318615
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-3H-purin-6-one
CAS Registry Number2140-77-4
SMILES
CNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H15N5O5/c1-12-11-14-8-5(9(20)15-11)13-3-16(8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15,20)/t4-,6-,7-,10-/m1/s1
InChI KeySLEHROROQDYRAW-KQYNXXCUSA-N
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
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not 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
logP-1.5ALOGPS
logP-1.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)2.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.96 m³·mol⁻¹ChemAxon
Polarizability28.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9170000000-23e6c75208d26fdba1f7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0089-9601700000-fc703aae8b6d6a4974edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-0325311279d987875e84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-e6ef13741f7f4dccbd5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-0de659a2e638147d57c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-6d26850eddc8183d02f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-1b6ec6169e212c49a64bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2a44663df36303389b18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-2900000000-c26900687cc1433c4dddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-0716675e30189c5c40b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0900000000-88909cd28924b82db6c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0920000000-bfd95b722408dc60bbf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-8fa2be1e1640632b908aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-ecafaa8f333c10b3b838View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-066u-9700000000-90bab7090f93d9ff10a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0960000000-f02a6cff92fcac500112View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-bf716bc83ef645366664View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0960000000-65b96211544ec1832e1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0940000000-14f44257677287f5052bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-fe9b56165c9d26491093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0900000000-2f57b0101465645d6551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0490000000-c15efc6d3614368fa118View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0910000000-7c27b8155c1a5068da22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xw-3900000000-a84717f336db9ad2d020View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0690000000-db7674b69c421aa74054View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0910000000-4bbef445b8d46b8d654bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-5900000000-d9115161a712f83a82caView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005862
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023782
KNApSAcK IDNot Available
Chemspider ID2299669
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7-Methylguanosine
METLIN IDNot Available
PubChem Compound3035422
PDB IDNot Available
ChEBI ID19702
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

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