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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2020-05-28 21:21:48 UTC
HMDB IDHMDB0002721
Secondary Accession Numbers
  • HMDB02721
Metabolite Identification
Common Name1-Methylinosine
DescriptionModified nucleotide found at position 37 in tRNA 3' to the anticodon of eukaryotic tRNA. Shown that sequences are forced to adopt a hairpin conformation if one of the central 6 nt is replaced by the corresponding methylated nucleotide, such as 1-methylguanosine. In Vivo synthesis: Inosine-37 in tRNA is synthesised by a hydrolytic deamination-type reaction, catalysed by distinct tRNA:adenosine deaminases.
Structure
Data?1582752254
Synonyms
ValueSource
m(1)IChEBI
N1-MethylinosineChEBI
1-Methyl-inosineHMDB
Chemical FormulaC11H14N4O5
Average Molecular Weight282.2527
Monoisotopic Molecular Weight282.096419578
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one
Traditional Name1-methylinosine
CAS Registry Number2140-73-0
SMILES
CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O
InChI Identifier
InChI=1S/C11H14N4O5/c1-14-3-13-9-6(10(14)19)12-4-15(9)11-8(18)7(17)5(2-16)20-11/h3-5,7-8,11,16-18H,2H2,1H3/t5-,7-,8-,11-/m1/s1
InChI KeyWJNGQIYEQLPJMN-IOSLPCCCSA-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
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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 Solubility16.8 g/LALOGPS
logP-1.5ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)1.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.23 m³·mol⁻¹ChemAxon
Polarizability27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9260000000-d61a359a55520b6ac4e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ayi-8888900000-435694604ab924019571Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-590c892f3434aeade64cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-5700e521158c2e2eebecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1900000000-1f7aae4adebc1e5e4609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0790000000-63ac267157492bd6dacfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d38b2649cc0a087967a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-54a59a321d15984ea2d3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0479 +/- 0.0138 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0680 +/- 0.022 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0716 +/- 0.021 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0606 +/- 0.018 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.073 +/- 0.027 uMAdult (>18 years old)Not SpecifiedNormal
    • Xu G, Enderle H, ...
details
BloodDetected and Quantified0.0553 +/- 0.016 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.13 +/- 0.18 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.200 +/- 0.721 uMAdult (>18 years old)Both
Uremia
details
UrineDetected and Quantified3.14 +/- 2.04 umol/mmol creatinineAdult (>18 years old)BothBreast cancer details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Breast cancer
  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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023053
KNApSAcK IDNot Available
Chemspider ID58605
KEGG Compound IDNot Available
BioCyc IDCPD0-1042
BiGG IDNot Available
Wikipedia Link1-Methylinosin
METLIN ID3780
PubChem Compound65095
PDB IDNot Available
ChEBI ID19065
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMiles, H. Todd. Preparation of 1-methylinosine. Journal of Organic Chemistry (1961), 26 4761-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reynaud C, Bruno C, Boullanger P, Grange J, Barbesti S, Niveleau A: Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. Cancer Lett. 1992 Jan 31;61(3):255-62. [PubMed:1739950 ]
  2. 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 ]
  3. Micura R, Pils W, Hobartner C, Grubmayr K, Ebert MO, Jaun B: Methylation of the nucleobases in RNA oligonucleotides mediates duplex-hairpin conversion. Nucleic Acids Res. 2001 Oct 1;29(19):3997-4005. [PubMed:11574682 ]
  4. Grosjean H, Auxilien S, Constantinesco F, Simon C, Corda Y, Becker HF, Foiret D, Morin A, Jin YX, Fournier M, Fourrey JL: Enzymatic conversion of adenosine to inosine and to N1-methylinosine in transfer RNAs: a review. Biochimie. 1996;78(6):488-501. [PubMed:8915538 ]
  5. Heldman DA, Grever MR, Trewyn RW: Differential excretion of modified nucleosides in adult acute leukemia. Blood. 1983 Feb;61(2):291-6. [PubMed:6571786 ]
  6. 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 ]