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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 11:31:47 UTC
Update Date2021-09-14 14:59:05 UTC
HMDB IDHMDB0011596
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 ).
Structure
Thumb
Synonyms
ValueSource
(7-(((4,5-cis-Dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine)HMDB
(Imidazol-4-yl)acetaldehydeHMDB
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
SMILES
NC1=NC(=O)C2=C(N1)N(C=C2CN[C@H]1C=C[C@H](O)[C@@H]1O)C1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16?/m0/s1
InChI KeyQQXQGKSPIMGUIZ-FSIZVHFJSA-N
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
Substituents
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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 ID35032074
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available