1-Methyladenosine (YMDB01575)

Identification
YMDB IDYMDB01575
Name1-Methyladenosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-Methyladenosine (m1A) is a modified nucleoside derived from adenosine and found in RNA. RNA modifications are present in many different types of cellular RNAs and a large number of enzymes and pathways that catalyze post-transcriptional RNA modifications are known. RNA modifications can play regulatory roles in cells, especially in response to stress conditions. 1-Methyladenosine is obtained in nature by post-transcriptional methylation of adenosine by methyl-1-adenosine transferase5 and it has a special role in t-RNA folding. [PMID: 21615108]
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS numberNot Available
WeightAverage: 283.2838
Monoisotopic: 283.128054057
InChI KeyQQBGTSSELNKRID-IOSLPCCCSA-N
InChIInChI=1S/C11H17N5O4/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(19)7(18)5(2-17)20-11/h4-5,7-8,11,17-19H,2-3,12H2,1H3/t5-,7-,8-,11-/m1/s1
IUPAC Name(2R,3R,4S,5R)-2-(6-amino-1-methyl-2,9-dihydro-1H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name1-methyl-adenosine
Chemical FormulaC11H17N5O4
SMILESCN1CN=C2N(C=NC2=C1N)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monosaccharide
  • N-substituted imidazole
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary aliphatic amine
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.42 g/LALOGPS
logP-2.2ALOGPS
logP-2.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.56ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area127.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.28 m³·mol⁻¹ChemAxon
Polarizability28.08 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-b3d29e95ee892fb651e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-48c964f45c1fe4b4c35cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f72-6900000000-a36ce71db8cbda578445JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0790000000-a27606aa33bfe491eddcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-49aa291f0ee9c991979cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-9f739d5bcfbe7cca3a37JSpectraViewer
References
References:
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16020
HMDB IDHMDB03331
Pubchem Compound ID27476
Kegg IDC02494
ChemSpider ID4573813
FOODB IDNot Available
Wikipedia IDN6-Methyladenosine
BioCyc IDNot Available