7-Cyano-7-carbaguanine (PAMDB001132)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001132
Identification
Name: 7-Cyano-7-carbaguanine
Description:7-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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 7-CN-7-deazaG
  • 7-cyano-7-carbaguanine
  • 7-Cyano-7-deazaguanine
  • PreQ0
Chemical Formula: C7H5N5O
Average Molecular Weight: 175.1475
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyrrolopyrimidines
Sub ClassNot Available
Direct Parent Pyrrolopyrimidines
Alternative Parents
Substituents
  • Pyrrolopyrimidine
  • Hydroxypyrimidine
  • Substituted pyrrole
  • Pyrimidine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.21 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.5 m3·mol-1ChemAxon
Polarizability15.88 Å3ChemAxon
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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