Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000403
Identification
Name: Queuine
Description:Queuine is a member of the chemical class known as Aminocyclitols and Derivatives. These are cyclitols with at least one hydroxyl group replace by an amino group. Queuine (Q) is a hypermodified base found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. The nucleoside of queuine is queuosine. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities. (WikiPedia)
Structure
Thumb
Synonyms:
  • 2-Amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo(2,3-D)pyrimidin-4-one
  • 7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine
  • 7AMe7DAGua
  • Base Q
  • Queuine
Chemical Formula: C12H15N5O3
Average Molecular Weight: 277.2792
Monoisotopic Molecular Weight: 277.117489371
InChI Key: WYROLENTHWJFLR-BHNWBGBOSA-N
InChI:InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1
CAS number: 72496-59-4
IUPAC Name:(1R,2S,5S)-5-[({4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]cyclopent-3-ene-1,2-diol
Traditional IUPAC Name: (1R,2S,5S)-5-[({4-hydroxy-2-imino-1H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]cyclopent-3-ene-1,2-diol
SMILES:O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyrrolopyrimidines
Sub ClassNot Available
Direct Parent Pyrrolopyrimidines
Alternative Parents
Substituents
  • Pyrrolopyrimidine
  • Hydroxypyrimidine
  • Aralkylamine
  • Substituted pyrrole
  • Pyrimidine
  • Heteroaromatic compound
  • Pyrrole
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.975PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.348 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.2ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.48ChemAxon
pKa (Strongest Basic)8.08ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area136.75 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.97 m3·mol-1ChemAxon
Polarizability27.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0490000000-79c2ee42b531999a48daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0940000000-3b8adbd9aa0d46707a89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-1cda697801b74c63eb78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-7248e6280feb27a6b9e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2790000000-6bcdd7a8145915cadc8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-4900000000-2ac324bda4a707569cceView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17433
HMDB IDHMDB01495
Pubchem Compound ID114881
Kegg IDC01449
ChemSpider ID1034
WikipediaQueuine
BioCyc IDNot Available
Ligand ExpoQEI