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7-Aminomethyl-7-carbaguanine (M2MDB001851)

Record Information
Version2.0
Creation Date2012-08-09 09:16:18 -0600
Update Date2015-06-03 17:21:33 -0600
Secondary Accession Numbers
  • ECMDB21456
Identification
Name:7-Aminomethyl-7-carbaguanine
Description7-Aminomethyl-7-carbaguanine is one of the precursors of nucleoside Q (queuosine) biosynthesis. It is a substrate for preQ1 synthase (EC 1.7.1.13) which catalyzes the NADPH-dependent reduction of 7-cyano-7-carbaguanine (preQ0) to 7-aminomethyl-7-carbaguanine (preQ1). More specifically, this enzyme catalyzes the chemical reaction
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 7-Aminomethyl-7-carbaguanine
  • 7-Aminomethyl-7-deazaguanine
  • PreQ1
Chemical Formula:C7H9N5O
Weight:Average: 179.1793
Monoisotopic: 179.080709935
InChI Key:MEYMBLGOKYDGLZ-UHFFFAOYSA-N
InChI:InChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)
CAS number:Not Available
IUPAC Name:2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
Traditional IUPAC Name:7-aminomethyl-7-deazaguanine
SMILES:NCC1=CNC2=C1C(=O)NC(N)=N2
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
  • Aralkylamine
  • Hydroxypyrimidine
  • Substituted pyrrole
  • Pyrimidine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.93 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.04ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.67 m³·mol⁻¹ChemAxon
Polarizability17.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPH
Guanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + Guanine
Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine
7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine
7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + Guanine
7 7-Aminomethyl-7-carbaguanine + NADP <>7 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine
Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vr-1900000000-6c74d2d331883324fbd8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-186cf56f77e8ac46162eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-e42a8c4daace1afde7aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-1900000000-d9d17cbc8d643eb3bb92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-7c00db685d48eeeaa166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-2900000000-8a8ba88dc9cf497add5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-8d2f3dc2af852732e95bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-640c17980dbf68c2f745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-ed2d82c910ac3948e2e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-110463c1e8dbf082afcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-056d9eb91af27afcf50dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-8b141eab907933d865b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0075-4900000000-b0875f15fc961a04cee6View in MoNA
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:
  • 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 ID45126
HMDB IDHMDB11690
Pubchem Compound ID171
Kegg IDC16675
ChemSpider ID166
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoPRF

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.