2.0 2012-05-31 14:37:42 -0600 2015-06-03 17:19:43 -0600 ECMDB20294 M2MDB001132 7-Cyano-7-carbaguanine 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. 7-CN-7-deazaG 7-cyano-7-carbaguanine 7-Cyano-7-deazaguanine PreQ0 C7H5N5O 175.1475 175.049409807 4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 7-cyano-7-deazaguanine OC1=NC(=N)NC2=C1C(=CN2)C#N 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) FMKSMYDYKXQYRV-UHFFFAOYSA-N Cytosol logp -0.10 ALOGPS logs -1.90 ALOGPS solubility 2.21e+00 g/l ALOGPS logp 0.11 ChemAxon pka_strongest_acidic -1.9 ChemAxon pka_strongest_basic 18.64 ChemAxon iupac 4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile ChemAxon average_mass 175.1475 ChemAxon mono_mass 175.049409807 ChemAxon smiles OC1=NC(=N)NC2=C1C(=CN2)C#N ChemAxon formula C7H5N5O ChemAxon 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) ChemAxon inchikey FMKSMYDYKXQYRV-UHFFFAOYSA-N ChemAxon polar_surface_area 108.05 ChemAxon refractivity 56.5 ChemAxon polarizability 15.88 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic Metabolic pathways eco01100 preQ0 metabolism PreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP. GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine. The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosine PW001893 Metabolic queuosine biosynthesis PWY-6700 preQ₀ biosynthesis PWY-6703 Specdb::CMs 1085309 Specdb::EiMs 2615 Specdb::NmrOneD 341228 Specdb::NmrOneD 341229 Specdb::NmrOneD 341230 Specdb::NmrOneD 341231 Specdb::NmrOneD 341232 Specdb::NmrOneD 341233 Specdb::NmrOneD 341234 Specdb::NmrOneD 341235 Specdb::NmrOneD 341236 Specdb::NmrOneD 341237 Specdb::NmrOneD 341238 Specdb::NmrOneD 341239 Specdb::NmrOneD 341240 Specdb::NmrOneD 341241 Specdb::NmrOneD 341242 Specdb::NmrOneD 341243 Specdb::NmrOneD 341244 Specdb::NmrOneD 341245 Specdb::NmrOneD 341246 Specdb::NmrOneD 341247 Specdb::MsMs 27977 Specdb::MsMs 27978 Specdb::MsMs 27979 Specdb::MsMs 34535 Specdb::MsMs 34536 Specdb::MsMs 34537 446357 393739 C15996 45075 7-CYANO-7-DEAZAGUANINE PQ0 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. 21097882 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. 22080510 NADPH-dependent 7-cyano-7-deazaguanine reductase Q46920 QUEF_ECOLI queF http://ecmdb.ca/proteins/Q46920.xml 7-cyano-7-deazaguanine synthase P77756 QUEC_ECOLI queC http://ecmdb.ca/proteins/P77756.xml 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 RXN-12093 preQ₁ + NADP < 7-Cyano-7-carbaguanine + NADPH + Hydrogen ion RXN0-4022 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 R07605 7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate <> 7-Cyano-7-carbaguanine + ADP + Phosphate + Water R09978 7-Deaza-7-carboxyguanine + Adenosine triphosphate + Ammonium > Water + Phosphate + Adenosine diphosphate + Hydrogen ion + 7-Cyano-7-carbaguanine + ADP PW_R005180 7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine PW_R005181 7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH > Queuine +2 NADP + Queuine PW_R005182 7 7-Aminomethyl-7-carbaguanine + NADP <>7 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion