1-Methylinosine (CHEM021860)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:14 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021860
Identification
Common Name1-Methylinosine
ClassSmall Molecule
DescriptionInosine carrying a methyl substituent at position 1 on the hypoxanthine ring.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
m(1)IChEBI
N1-MethylinosineChEBI
1-Methyl-inosineHMDB
Chemical FormulaC11H14N4O5
Average Molecular Mass282.253 g/mol
Monoisotopic Mass282.096 g/mol
CAS Registry Number2140-73-0
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
SMILESCN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-d3116843b691b79a17a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-4c5f22a621f1bf5edca3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-08bd7a023e7c71d7fa14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0950000000-e29272a7e2cfc8cd35b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5eddb3d0c408b01a8037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-7f4e88398d5f4a1895ceSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002721
FooDB IDFDB023053
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD0-1042
METLIN ID3780
PDB IDNot Available
Wikipedia Link1-Methylinosin
Chemspider ID58605
ChEBI ID19065
PubChem Compound ID65095
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1262659
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1873911
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3132457
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4720877
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=5765842
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7183961
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=723886
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7392649
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7501451
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=908140
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9376997
13. Miles, H. Todd. Preparation of 1-methylinosine. Journal of Organic Chemistry (1961), 26 4761-2.
14. 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.
15. 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.
16. 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.
17. 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.
18. Heldman DA, Grever MR, Trewyn RW: Differential excretion of modified nucleosides in adult acute leukemia. Blood. 1983 Feb;61(2):291-6.
19. 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.