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Record Information
StatusExpected but not Quantified
Creation Date2009-01-29 11:31:47 UTC
Update Date2020-02-26 21:35:27 UTC
Secondary Accession Numbers
  • HMDB11596
Metabolite Identification
Common NameQueuosine
DescriptionQueuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes. Originally identified in E. coli, queuosine was found to occupy the first anticodon position of tRNAs for histidine, aspartic acid, asparagine and tyrosine. The first anticodon position pairs with the third "wobble" position in codons, and queuosine improves accuracy of translation. Synthesis of queuosine begins with GTP. In bacteria, two classes of riboswitch are known to regulate genes that are involved in the synthesis or transport of pre-queuosine1, a precursor to queuosine: PreQ1-I riboswitches and PreQ1-II riboswitches (Wikipedia).
Chemical FormulaC17H23N5O7
Average Molecular Weight409.3938
Monoisotopic Molecular Weight409.159748115
IUPAC Name2-amino-7-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
Traditional Name2-amino-7-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H-pyrrolo[2,3-d]pyrimidin-4-one
CAS Registry Number57072-36-3
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrrolopyrimidine nucleosides and nucleotides
Sub ClassNot Available
Direct ParentPyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
  • Pyrrolopyrimidine ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyrrolopyrimidine
  • Pyrrolo[2,3-d]pyrimidine
  • Aminopyrimidine
  • Aralkylamine
  • Pyrimidone
  • Monosaccharide
  • Substituted pyrrole
  • Pyrimidine
  • Pyrrole
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Secondary aliphatic amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility7.96 g/LALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)7.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area194.82 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.56 m³·mol⁻¹ChemAxon
Polarizability40.65 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bd-6019000000-e97e68fb7379782ccbb0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5800029000-6c77c52dfdcc39c7eb28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0192300000-6d96e8b639678c99d0d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1691000000-524209d74b19824bc972Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-2690000000-5c2418d2190c7fa5e128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0365900000-b72401c13028067c334eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-1391000000-0ccfb7d7c8d18f40744bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f92-0690000000-c42312dc0243346876eeSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028309
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQueuosine
METLIN IDNot Available
PubChem Compound137185891
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available