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
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:
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 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
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

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.
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.