Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Queuine (M2MDB000403)

Record Information
Version2.0
Creation Date2012-05-31 13:53:37 -0600
Update Date2015-09-17 15:41:12 -0600
Secondary Accession Numbers
  • ECMDB01495
Identification
Name:Queuine
DescriptionQueuine 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 277.2792
Monoisotopic: 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
Description belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolopyrimidines
Sub ClassPyrrolo[2,3-d]pyrimidines
Direct ParentPyrrolo[2,3-d]pyrimidines
Alternative Parents
Substituents
  • Pyrrolo[2,3-d]pyrimidine
  • Hydroxypyrimidine
  • Aralkylamine
  • Pyrimidine
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.35 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.97 m³·mol⁻¹ChemAxon
Polarizability27.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3 Hydrogen ion + 2 NADPH + 7-Cyano-7-carbaguanine >2 NADP + Queuine
Guanine(34) in tRNA + Queuine > queuosine(34) in tRNA + Guanine
Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH > Queuine +2 NADP + Queuine
Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine
Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine
SMPDB Pathways:
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
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

Enzymes

Protein Details
1. Queuine tRNA-ribosyltransferase
General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Exchanges the guanine residue with 7-aminomethyl-7- deazaguanine in tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr). After this exchange, a cyclopentendiol moiety is attached to the 7-aminomethyl group of 7-deazaguanine, resulting in the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis- dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine)
Gene Name:
tgt
Uniprot ID:
P0A847
Molecular weight:
42593
Reactions
[tRNA]-guanine + queuine = [tRNA]-queuine + guanine.
[tRNA]-guanine + 7-aminomethyl-7-carbaguanine = [tRNA]-7-aminomethyl-7-carbaguanine + guanine.
Protein Details
2. NADPH-dependent 7-cyano-7-deazaguanine reductase
General function:
Involved in oxidoreductase activity, acting on other nitrogenous compounds as donors, with NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of 7-cyano-7- deazaguanine (preQ0) to 7-aminomethyl-7-deazaguanine (preQ1)
Gene Name:
queF
Uniprot ID:
Q46920
Molecular weight:
32587
Reactions
7-aminomethyl-7-carbaguanine + 2 NADP(+) = 7-cyano-7-carbaguanine + 2 NADPH.