2.0 2012-07-30 14:54:47 -0600 2015-06-03 17:20:49 -0600 ECMDB21183 M2MDB001592 7-Deaza-7-carboxyguanine 7-deaza-7-carboxyguanine 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. 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylate 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylic acid 7-Deaza-7-carboxyguanine C7H6N4O3 194.1475 194.043990078 2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid 2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid [H]OC(=O)C1=C([H])N([H])C2=C1C(=O)N=C(N([H])[H])N2[H] InChI=1S/C7H6N4O3/c8-7-10-4-3(5(12)11-7)2(1-9-4)6(13)14/h1H,(H,13,14)(H4,8,9,10,11,12) XIUIRSLBMMTDSK-UHFFFAOYSA-N Cytosol logp -0.51 ALOGPS logs -1.82 ALOGPS solubility 2.96e+00 g/l ALOGPS logp -0.16 ChemAxon pka_strongest_acidic 5.21 ChemAxon pka_strongest_basic 0.05 ChemAxon iupac 2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid ChemAxon average_mass 194.1475 ChemAxon mono_mass 194.043990078 ChemAxon smiles [H]OC(=O)C1=C([H])N([H])C2=C1C(=O)N=C(N([H])[H])N2[H] ChemAxon formula C7H6N4O3 ChemAxon inchi InChI=1S/C7H6N4O3/c8-7-10-4-3(5(12)11-7)2(1-9-4)6(13)14/h1H,(H,13,14)(H4,8,9,10,11,12) ChemAxon inchikey XIUIRSLBMMTDSK-UHFFFAOYSA-N ChemAxon polar_surface_area 120.57 ChemAxon refractivity 47.02 ChemAxon polarizability 17.1 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 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 Specdb::CMs 1084200 Specdb::EiMs 3079 Specdb::NmrOneD 313761 Specdb::NmrOneD 313762 Specdb::NmrOneD 313763 Specdb::NmrOneD 313764 Specdb::NmrOneD 313765 Specdb::NmrOneD 313766 Specdb::NmrOneD 313767 Specdb::NmrOneD 313768 Specdb::NmrOneD 313769 Specdb::NmrOneD 313770 Specdb::NmrOneD 313771 Specdb::NmrOneD 313772 Specdb::NmrOneD 313773 Specdb::NmrOneD 313774 Specdb::NmrOneD 313775 Specdb::NmrOneD 313776 Specdb::NmrOneD 313777 Specdb::NmrOneD 313778 Specdb::NmrOneD 313779 Specdb::NmrOneD 313780 Specdb::MsMs 24710 Specdb::MsMs 24711 Specdb::MsMs 24712 Specdb::MsMs 31268 Specdb::MsMs 31269 Specdb::MsMs 31270 13344694 26332127 C20248 61125 7-cyano-7-deazaguanine synthase P77756 QUEC_ECOLI queC http://ecmdb.ca/proteins/P77756.xml 7-carboxy-7-deazaguanine synthase; queosine biosynthesis P64554 queE http://ecmdb.ca/proteins/P64554.xml Adenosine triphosphate + 7-Deaza-7-carboxyguanine + Ammonium > ADP + Hydrogen ion + Water + Phosphate + 7-Cyano-7-carbaguanine 7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate > 7-Cyano-7-carbaguanine + ADP + Inorganic phosphate + Water 6-Carboxy-5,6,7,8-tetrahydropterin > 7-Deaza-7-carboxyguanine + Ammonia 7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate <> 7-Cyano-7-carbaguanine + ADP + Phosphate + Water R09978 6-Carboxy-5,6,7,8-tetrahydropterin <> 7-Carboxy-7-carbaguanine + Ammonia + 7-Deaza-7-carboxyguanine R10002 7-Deaza-7-carboxyguanine + Adenosine triphosphate + Ammonium > Water + Phosphate + Adenosine diphosphate + Hydrogen ion + 7-Cyano-7-carbaguanine + ADP PW_R005180