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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:56 UTC
HMDB IDHMDB01563
Secondary Accession NumbersNone
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 and they have been proposed as tumour markers. Their. measurement could provide a non-invasive diagnostic method, be helpful in the identification of different cancers and in the monitoring of therapeutic effects. PMID: 9129323 .
Structure
Thumb
Synonyms
ValueSource
m1gChEBI
N1-MethylguanosineChEBI
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 KeyInChIKey=UTAIYTHAJQNQDW-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These 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 ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Purinone
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and 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
Water Solubility16.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.52 m3·mol-1ChemAxon
Polarizability28.17 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.046 +/- 0.019 uMAdult (>18 years old)BothNormal 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. [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. [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. [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
NuGOwiki LinkHMDB01563
Metagene LinkHMDB01563
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. [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. [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. [11539621 ]