Record Information
Version2.0
Creation Date2012-10-10 12:22:14 -0600
Update Date2015-06-03 17:26:10 -0600
Secondary Accession Numbers
  • ECMDB23210
Identification
Name:7-Aminomethyl-7-deazaguanosine
Description7-Aminomethyl-7-deazaguanosine is an intermediate in tRNA charging and tRNA queosine synthesis. It is a substrate for S-adenosylmethionine:tRNA ribosyltransferase-isomerase which catalyzes the reaction: S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine
Structure
Thumb
Synonyms:
  • 2-amino-5-(aminomethyl)-7-(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl-1H-pyrrolo2,3-dpyrimidin-4-one
Chemical Formula:C12H17N5O5
Weight:Average: 311.2939
Monoisotopic: 311.122968679
InChI Key:SOEYIPCQNRSIAV-IOSLPCCCSA-N
InChI:InChI=1S/C12H17N5O5/c13-1-4-2-17(9-6(4)10(21)16-12(14)15-9)11-8(20)7(19)5(3-18)22-11/h2,5,7-8,11,18-20H,1,3,13H2,(H3,14,15,16,21)/t5-,7-,8-,11-/m1/s1
CAS number:Not Available
IUPAC Name:(2R,3R,4S,5R)-2-[5-(aminomethyl)-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name:(2R,3R,4S,5R)-2-[5-(aminomethyl)-4-hydroxy-2-imino-1H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol
SMILES:[H][C@]1(CO)O[C@@]([H])(N2C=C(CN)C3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description 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
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • Pyrrolo[2,3-d]pyrimidine
  • Pyrrolopyrimidine
  • Aralkylamine
  • Pyrimidone
  • Aminopyrimidine
  • Substituted pyrrole
  • Pyrimidine
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Pyrrole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.19 g/LALOGPS
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.42ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area169.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.85 m³·mol⁻¹ChemAxon
Polarizability30.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_19) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0953000000-af197944438988b92a89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0910000000-2c0ac164bb86fde3fe94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1900000000-5f5b3d2e599e1280a8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0869000000-26d28ba08bd5d9e4712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0910000000-de08ec2d63ac2b77f4f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01sa-0900000000-e8ee218d0e15e35858bcView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID191792
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Translation, ribosomal structure and biogenesis
Specific function:
Transfers and isomerizes the ribose moiety from AdoMet to the 7-aminomethyl group of 7-deazaguanine (preQ1-tRNA) to give epoxyqueuosine (oQ-tRNA)
Gene Name:
queA
Uniprot ID:
P0A7F9
Molecular weight:
39430
Reactions
S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine.