2.0 2012-10-10 12:22:14 -0600 2015-06-03 17:26:10 -0600 ECMDB23210 M2MDB003600 7-Aminomethyl-7-deazaguanosine 7-Aminomethyl-7-deazaguanosine is an intermediate in tRNA charging and tRNA queosine synthesis. It is a substrate for S-adenosylmethionine:tRNA ribosyltransferase-isomerase which catalyzes the reaction: S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine 2-amino-5-(aminomethyl)-7-(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl-1H-pyrrolo2,3-dpyrimidin-4-one C12H17N5O5 311.2939 311.122968679 (2R,3R,4S,5R)-2-[5-(aminomethyl)-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol (2R,3R,4S,5R)-2-[5-(aminomethyl)-4-hydroxy-2-imino-1H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol [H][C@]1(CO)O[C@@]([H])(N2C=C(CN)C3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O InChI=1S/C12H17N5O5/c13-1-4-2-17(9-6(4)10(21)16-12(14)15-9)11-8(20)7(19)5(3-18)22-11/h2,5,7-8,11,18-20H,1,3,13H2,(H3,14,15,16,21)/t5-,7-,8-,11-/m1/s1 SOEYIPCQNRSIAV-IOSLPCCCSA-N logp -1.78 ALOGPS logs -1.58 ALOGPS solubility 8.19e+00 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 7.42 ChemAxon pka_strongest_basic 9.09 ChemAxon iupac (2R,3R,4S,5R)-2-[5-(aminomethyl)-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol ChemAxon average_mass 311.2939 ChemAxon mono_mass 311.122968679 ChemAxon smiles [H][C@]1(CO)O[C@@]([H])(N2C=C(CN)C3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O ChemAxon formula C12H17N5O5 ChemAxon inchi InChI=1S/C12H17N5O5/c13-1-4-2-17(9-6(4)10(21)16-12(14)15-9)11-8(20)7(19)5(3-18)22-11/h2,5,7-8,11,18-20H,1,3,13H2,(H3,14,15,16,21)/t5-,7-,8-,11-/m1/s1 ChemAxon inchikey SOEYIPCQNRSIAV-IOSLPCCCSA-N ChemAxon polar_surface_area 169.34 ChemAxon refractivity 85.85 ChemAxon polarizability 30.14 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon 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 1083418 Specdb::EiMs 4107 Specdb::NmrOneD 303911 Specdb::NmrOneD 303912 Specdb::NmrOneD 303913 Specdb::NmrOneD 303914 Specdb::NmrOneD 303915 Specdb::NmrOneD 303916 Specdb::NmrOneD 303917 Specdb::NmrOneD 303918 Specdb::NmrOneD 303919 Specdb::NmrOneD 303920 Specdb::NmrOneD 303921 Specdb::NmrOneD 303922 Specdb::NmrOneD 303923 Specdb::NmrOneD 303924 Specdb::NmrOneD 303925 Specdb::NmrOneD 303926 Specdb::NmrOneD 303927 Specdb::NmrOneD 303928 Specdb::NmrOneD 303929 Specdb::NmrOneD 303930 Specdb::MsMs 24446 Specdb::MsMs 24447 Specdb::MsMs 24448 Specdb::MsMs 31004 Specdb::MsMs 31005 Specdb::MsMs 31006 191792 S-adenosylmethionine:tRNA ribosyltransferase-isomerase P0A7F9 QUEA_ECOLI queA http://ecmdb.ca/proteins/P0A7F9.xml S-adenosyl-L-methionine + 7-Aminomethyl-7-deazaguanosine > L-Methionine + Adenine + epoxyqueuosine