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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:30 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
Data?1582752205
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
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
  • 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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available163.51631661259
DarkChem[M-H]-PredictedNot Available160.78531661259
AllCCS[M+H]+PredictedNot Available165.10232859911
AllCCS[M-H]-PredictedNot Available163.71532859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Queuine,1TMS,#12889.9683https://arxiv.org/abs/1905.12712
Queuine,1TMS,#22896.334https://arxiv.org/abs/1905.12712
Queuine,1TMS,#32885.325https://arxiv.org/abs/1905.12712
Queuine,1TMS,#42840.4036https://arxiv.org/abs/1905.12712
Queuine,1TMS,#52857.681https://arxiv.org/abs/1905.12712
Queuine,1TMS,#62822.393https://arxiv.org/abs/1905.12712
Queuine,1TMS,#72819.782https://arxiv.org/abs/1905.12712
Queuine,2TMS,#12854.523https://arxiv.org/abs/1905.12712
Queuine,2TMS,#22842.324https://arxiv.org/abs/1905.12712
Queuine,2TMS,#32804.189https://arxiv.org/abs/1905.12712
Queuine,2TMS,#42794.8916https://arxiv.org/abs/1905.12712
Queuine,2TMS,#52789.164https://arxiv.org/abs/1905.12712
Queuine,2TMS,#62852.6255https://arxiv.org/abs/1905.12712
Queuine,2TMS,#72855.3616https://arxiv.org/abs/1905.12712
Queuine,2TMS,#82812.4102https://arxiv.org/abs/1905.12712
Queuine,2TMS,#92811.8735https://arxiv.org/abs/1905.12712
Queuine,2TMS,#102793.4766https://arxiv.org/abs/1905.12712
Queuine,2TMS,#112869.895https://arxiv.org/abs/1905.12712
Queuine,2TMS,#122814.5867https://arxiv.org/abs/1905.12712
Queuine,2TMS,#132802.0596https://arxiv.org/abs/1905.12712
Queuine,2TMS,#142788.3818https://arxiv.org/abs/1905.12712
Queuine,2TMS,#152853.3857https://arxiv.org/abs/1905.12712
Queuine,2TMS,#162830.8645https://arxiv.org/abs/1905.12712
Queuine,2TMS,#172779.4504https://arxiv.org/abs/1905.12712
Queuine,2TMS,#182794.7954https://arxiv.org/abs/1905.12712
Queuine,2TMS,#192816.15https://arxiv.org/abs/1905.12712
Queuine,2TMS,#202836.4993https://arxiv.org/abs/1905.12712
Queuine,2TMS,#212808.266https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#13105.2231https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#23112.1707https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#33115.8062https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#43073.705https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#53082.5896https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#63083.8596https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#73019.465https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#13257.8513https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#23232.4897https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#33222.5918https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#43197.7332https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#53187.9863https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#63265.2778https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#73240.3633https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#83235.9941https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#93219.2524https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#103192.387https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#113282.495https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#123262.5051https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#133219.459https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#143197.4685https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#153269.6382https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#163312.8916https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#173223.551https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#183262.356https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#193265.7437https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#203295.319https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#213240.6807https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mk-5090000000-652d0769b52b975c51572017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0pkc-9008300000-f8b2fbd8eff39e3fc5592017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0490000000-fb52b5c6a2d47b0519942017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0930000000-fbf4852f9df58f0e7c7a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-e9fb13544e19e8acbdc52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-d43c7510712f48a509a92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-5690000000-c52e490ff589e882ed092017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-6900000000-80c4828f9526f89180432017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0490000000-237adb25ec0428e0dd222021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0980000000-51b408b7c28c2878bc582021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0910000000-0bc9779e624e8314aab52021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0970000000-89efef47c25a5bb1e1622021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-0890000000-06643dd86a98e7fb7a9e2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-062fe840765b80e244612021-09-09View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
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
FooDB IDFDB022654
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01449
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQueuine
METLIN ID6279
PubChem Compound53477731
PDB IDNot Available
ChEBI ID17433
Food Biomarker OntologyNot Available
VMH IDM02820
MarkerDB IDNot Available
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