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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-29 11:31:47 UTC
Update Date2017-12-07 02:31:50 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
DescriptionThis compound 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
Disposition

Source:

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 Solubility7.96 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-1.7ALOGPS
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
Bioavailability0ChemAxon
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, Positivesplash10-00bd-6019000000-e97e68fb7379782ccbb0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5800029000-6c77c52dfdcc39c7eb28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0192300000-6d96e8b639678c99d0d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1691000000-524209d74b19824bc972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-2690000000-5c2418d2190c7fa5e128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0365900000-b72401c13028067c334eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-1391000000-0ccfb7d7c8d18f40744bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f92-0690000000-c42312dc0243346876eeView in MoNA
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
FoodDB IDFDB028309
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-8536
BiGG IDNot Available
Wikipedia LinkQueuosine
METLIN IDNot Available
PubChem Compound53481002
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available