Showing metabocard for 1-Methylguanosine (BMDB0001563)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:42 UTC
Update Date2020-04-22 15:08:43 UTC
BMDB IDBMDB0001563
Secondary Accession Numbers
  • BMDB01563
Metabolite Identification
Common Name1-Methylguanosine
Description1-Methylguanosine, also known as M1G, 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 1-Methylguanosine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
m1gChEBI
N1-MethylguanosineChEBI
N-MethylguanosineMeSH
1-Methyl-guanosineHMDB
MethylguanosineHMDB
TRMD ProteinHMDB
Chemical FormulaC11H15N5O5
Average Molecular Weight297.2673
Monoisotopic Molecular Weight297.107318615
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one
Traditional Name1-methylguanosine
CAS Registry Number2140-65-0
SMILES
CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O
InChI Identifier
InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1
InChI KeyUTAIYTHAJQNQDW-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
  • Purinone
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Vinylogous amide
  • Lactam
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • 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-1.8ALOGPS
logP-2.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)1.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.52 m³·mol⁻¹ChemAxon
Polarizability28.17 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, Positivesplash10-0avr-9160000000-c71871a3455821cc0cd8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000t-6902400000-f62364e1c258d1b21910View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-83049daf172a0028ef3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-297efbbdd4c56947d85aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-06sj-0900000000-c3b78851ce459f2b0533View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0900000000-ac1e4f86f920ef0213ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-dbbf8ee001ac7ebe8695View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0910000000-74105b75d5b6ac019686View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900000000-1a00daf15f672985739aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udj-0960000000-d5cca20daa4759338cf8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-76bb8e0e68de58eab7cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-5900000000-e057b071aa699b98597cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0961000000-b3371b576dbf1f20bc3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0900000000-e12157cd4c291c524ecaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0951000000-066a7ef362ef49118035View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-ac243405a8007cad3850View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-206489ed223c9cc32613View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-1900000000-46402612942543fd8d3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0940000000-cdf8a532f9a4c0deef48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-e8970970eb1ddb9b37bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-0900000000-f7ea94f03c9a16bf02d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0490000000-97864ef8e1af3fce3c34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0910000000-d1f62b75fc81d9c17e96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1900000000-6dceb96152f42447d0bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-7f20cf9333bbb1eb98e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0900000000-692fbb8505828e0608d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-59ff254f4a4342a7d6b1View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
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
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Kurt J. Boudonck,...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001563
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022690
KNApSAcK IDNot Available
Chemspider ID86996
KEGG Compound IDC04545
BioCyc IDCPD0-1043
BiGG IDNot Available
Wikipedia Link7-Methylguanosine
METLIN ID6324
PubChem Compound96373
PDB IDNot Available
ChEBI ID19062
References
Synthesis ReferenceErmolinsky Boris S; Efimtseva Ekaterina V; Alexeev Cyrill S; Mikhailov Sergey N; Balzarini Jan; De Clercq Erik Dinucleoside monophosphates containing AZT and 1-methyladenosine or 7-methylguanosine. Nucleosides, nucleotides & nucleic acids (2003), 22(5-8), 853-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

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