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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 07:58:57 UTC
HMDB IDHMDB0001495
Secondary Accession Numbers
  • HMDB01495
Metabolite Identification
Common NameQueuine
DescriptionQueuine is a highly modified derivative of guanine found in the first position of the anticodon of the transfer RNAs for asp, asn, his and tyr. The original transcripts of these tRNAs contain guanine in this position. All organisms with the exception of yeast and mycoplasma contain queuine. Bacteria synthesize queuine but it cannot be synthesized by higher mammals. Significant amounts of free queuine are present in common plant and animal food products. (PMID 9016755 ).
Structure
Thumb
Synonyms
ValueSource
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-oneHMDB
7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanineHMDB
Base QHMDB
Chemical FormulaC12H15N5O3
Average Molecular Weight277.2792
Monoisotopic Molecular Weight277.117489371
IUPAC Name5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
Traditional Name5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,3H,7H-pyrrolo[2,3-d]pyrimidin-4-one
CAS Registry Number72496-59-4
SMILES
O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O
InChI Identifier
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
InChI KeyWYROLENTHWJFLR-BHNWBGBOSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Aminopyrimidine
  • Pyrimidone
  • Aralkylamine
  • Pyrimidine
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility0.31 g/LALOGPS
logP-1.1ALOGPS
logP-0.71ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.11ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area133.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.45 m³·mol⁻¹ChemAxon
Polarizability27.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-05mk-5090000000-652d0769b52b975c5157View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0pkc-9008300000-f8b2fbd8eff39e3fc559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0490000000-fb52b5c6a2d47b051994View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0930000000-fbf4852f9df58f0e7c7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-e9fb13544e19e8acbdc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-d43c7510712f48a509a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-5690000000-c52e490ff589e882ed09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-6900000000-80c4828f9526f8918043View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Amniotic Fluid
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.105 uMNot SpecifiedFemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022654
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01449
BioCyc IDQUEUINE
BiGG IDNot Available
Wikipedia LinkQueuine
METLIN ID6279
PubChem Compound53477731
PDB IDNot Available
ChEBI ID17433
References
Synthesis ReferenceAkimoto, Hiroshi; Imamiya, Eiko; Hitaka, Takenori; Nomura, Hiroaki; Nishimura, Susumu. Synthesis of queuine, the base of naturally occurring hypermodified nucleoside (queuosine), and its analogs. Journal of the Chemical Society, Perkin Transactions 1: Org
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Baranowski W, Tomaszewski J, Keith G: Unusual deficiency of the modified purine base queuine in transfer ribonucleic acid from the human placenta as tested by enzymatic assay. Am J Obstet Gynecol. 1993 Sep;169(3):581-2. [PubMed:8372867 ]
  2. Marks T, Farkas WR: Effects of a diet deficient in tyrosine and queuine on germfree mice. Biochem Biophys Res Commun. 1997 Jan 13;230(2):233-7. [PubMed:9016755 ]

Enzymes

General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Interacts with QTRTD1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:
QTRT1
Uniprot ID:
Q9BXR0
Molecular weight:
44047.3
Reactions
Guanine(34) in tRNA + Queuine → queuosine(34) in tRNA + Guaninedetails
tRNA guanine + Queuine → tRNA queuine + Guaninedetails
General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Interacts with QTRT1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:
QTRTD1
Uniprot ID:
Q9H974
Molecular weight:
48203.07
Reactions
Guanine(34) in tRNA + Queuine → queuosine(34) in tRNA + Guaninedetails
tRNA guanine + Queuine → tRNA queuine + Guaninedetails