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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:45:38 UTC
HMDB IDHMDB0001563
Secondary Accession Numbers
  • HMDB01563
Metabolite Identification
Common Name1-Methylguanosine
Description1-Methylguanosine is a methylated nucleoside. It is known that some modified, especially methylated, nucleosides originating from RNA degradation are excreted in abnormal levels in the urine of patients with malignant tumours. These nucleosides have been proposed as tumour markers. Their measurement could provide a non-invasive diagnostic method, help identify different cancers, and monitor any therapeutic effects (PMID: 9129323 ).
Structure
Thumb
Synonyms
ValueSource
m1gChEBI
N1-MethylguanosineChEBI
1-Methyl-guanosineHMDB
MethylguanosineHMDB
TRMD ProteinHMDB
N-MethylguanosineMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Pentose monosaccharide
  • Purinone
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Monosaccharide
  • Pyrimidine
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Oxolane
  • 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
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-1.8ALOGPS
logP-2.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)1.98ChemAxon
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
Bioavailability1ChemAxon
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 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Breast Milk
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.046 +/- 0.019 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified0.68+/- 0.18 uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.86 +/- 0.22 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.4 +/- 0.7 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.099 +/- 0.021 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.078 +/- 0.010 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.140 +/- 0.020 uMAdult (>18 years old)BothUremia details
BloodDetected and Quantified0.120 +/- 0.020 uMAdult (>18 years old)Both
Uremia
details
UrineDetected and Quantified0.97 +/- 0.33 umol/mmol creatinineAdult (>18 years old)Not SpecifiedBreast cancer details
UrineDetected and Quantified9.5 +/- 0.8 umol/mmol creatinineAdult (>18 years old)BothUremia details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Zheng YF, Kong HW, Xiong JH, Lv S, Xu GW: Clinical significance and prognostic value of urinary nucleosides in breast cancer patients. Clin Biochem. 2005 Jan;38(1):24-30. [PubMed:15607313 ]
Kidney disease
  1. Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Uremia
  1. Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022690
KNApSAcK IDNot Available
Chemspider ID86996
KEGG Compound IDC04545
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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)Download (PDF)
General References
  1. Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
  2. Heldman DA, Grever MR, Miser JS, Trewyn RW: Relationship of urinary excretion of modified nucleosides to disease status in childhood acute lymphoblastic leukemia. J Natl Cancer Inst. 1983 Aug;71(2):269-73. [PubMed:6576186 ]
  3. Szabo LD, Keresztes P, Pallos JP, Csato E, Predmerszky T: Study of nucleic acid metabolism in two astronauts. Adv Space Res. 1984;4(10):15-8. [PubMed:11539621 ]