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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2018-05-19 22:04:49 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
Thumb
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
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 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)1.58ChemAxon
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
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, Positivesplash10-05fu-9260000000-d61a359a55520b6ac4e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ayi-8888900000-435694604ab924019571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-590c892f3434aeade64cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-5700e521158c2e2eebecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1900000000-1f7aae4adebc1e5e4609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0790000000-63ac267157492bd6dacfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d38b2649cc0a087967a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-54a59a321d15984ea2d3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified3.14 +/- 2.04 umol/mmol creatinineAdult (>18 years old)BothCancer details
Associated Disorders and Diseases
Disease References
Thyroid 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
FoodDB 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
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. 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. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Heldman DA, Grever MR, Trewyn RW: Differential excretion of modified nucleosides in adult acute leukemia. Blood. 1983 Feb;61(2):291-6. [PubMed:6571786 ]