7-Cyano-7-carbaguanine (ECMDB20294) (M2MDB001132)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (506)
Record Information
Version2.0
Creation Date2012-05-31 14:37:42 -0600
Update Date2015-06-03 17:19:43 -0600
Secondary Accession Numbers
  • ECMDB20294
Identification
Name:7-Cyano-7-carbaguanine
Description7-cyano-7-carbaguanine is a member of the chemical class known as Pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. This compound is involved in queuosine biosynthesis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 7-CN-7-deazaG
  • 7-cyano-7-carbaguanine
  • 7-Cyano-7-deazaguanine
  • PreQ0
Chemical Formula:C7H5N5O
Weight:Average: 175.1475
Monoisotopic: 175.049409807
InChI Key:FMKSMYDYKXQYRV-UHFFFAOYSA-N
InChI:InChI=1S/C7H5N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,(H4,9,10,11,12,13)
CAS number:Not Available
IUPAC Name:4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Traditional IUPAC Name:7-cyano-7-deazaguanine
SMILES:OC1=NC(=N)NC2=C1C(=CN2)C#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
  • Pyrimidine
  • Substituted pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrole
  • Carbonitrile
  • Nitrile
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP-0.1ALOGPS
logP0.11ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)18.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.05 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.5 m³·mol⁻¹ChemAxon
Polarizability15.88 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + 7-Deaza-7-carboxyguanine + Ammonium > ADP + Hydrogen ion + Water + Phosphate + 7-Cyano-7-carbaguanine
3 Hydrogen ion + 2 NADPH + 7-Cyano-7-carbaguanine >2 NADP + Queuine
7-carboxy-7-deazaguanine + Ammonia + Adenosine triphosphate > 7-Cyano-7-carbaguanine + ADP + Phosphate + Water
preQ<sub>1</sub> + NADP < 7-Cyano-7-carbaguanine + NADPH + Hydrogen ion
7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate > 7-Cyano-7-carbaguanine + ADP + Inorganic phosphate + Water
7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPH
7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate <> 7-Cyano-7-carbaguanine + ADP + Phosphate + Water
7-Deaza-7-carboxyguanine + Adenosine triphosphate + Ammonium > Water + Phosphate + Adenosine diphosphate + Hydrogen ion + 7-Cyano-7-carbaguanine + ADP
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH > Queuine +2 NADP + Queuine
7 7-Aminomethyl-7-carbaguanine + NADP <>7 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-af2ae62c4c215361ecedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0900000000-9e5f5f67428ff03e8e27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-370668da5ccac92b10dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-03d09ff2a0e7426078a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-38453df754a7089d2db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-2a2f03d4b6dc173ec6adView 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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID45075
HMDB IDNot Available
Pubchem Compound ID446357
Kegg IDC15996
ChemSpider ID393739
Wikipedia IDNot Available
BioCyc ID7-CYANO-7-DEAZAGUANINE
EcoCyc ID7-CYANO-7-DEAZAGUANINE
Ligand ExpoPQ0

Enzymes

Protein Details
1. 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.
Protein Details
2. 7-cyano-7-deazaguanine synthase
General function:
Involved in argininosuccinate synthase activity
Specific function:
Catalyzes the ATP-dependent conversion of 7-carboxy-7- deazaguanine (CDG) to 7-cyano-7-deazaguanine (preQ(0))
Gene Name:
queC
Uniprot ID:
P77756
Molecular weight:
25514
Reactions
7-carboxy-7-carbaguanine + NH(3) + ATP = 7-cyano-7-carbaguanine + ADP + phosphate + H(2)O.