2.0 2012-10-10 12:21:06 -0600 2015-06-03 17:26:07 -0600 ECMDB23186 M2MDB003576 epoxyqueuosine Epoxyqueuosine is an intermediate in queosine biosynthesis. Queuosine is an important 7-deazapurine-modified nucleoside that is present in certain tRNAs in bacteria and most eukaryotes. Eposyqueosiine is a subsstrate for Epoxyqueuosine reductase catalyzes the final step in the de novo synthesis of queuosine, the anticodon loop modification found in tRNA(Asp), tRNA(Asn), tRNA(His), and tRNA(Tyr) 2-amino-7-(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl-5-(3,4-dihydroxy-6-oxabicyclo3.1.0hexan-2-yl)aminomethyl-1H-pyrrolo2,3-dpyrimidin-4-one C17H23N5O8 425.3932 425.154662737 4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol 4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol [H]C12OC1([H])C([H])(NCC1=CN(C3=C1C(O)=NC(=N)N3)[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O)C([H])(O)C2([H])O InChI=1S/C17H23N5O8/c18-17-20-14-6(15(28)21-17)4(1-19-7-9(25)10(26)13-12(7)30-13)2-22(14)16-11(27)8(24)5(3-23)29-16/h2,5,7-13,16,19,23-27H,1,3H2,(H3,18,20,21,28)/t5-,7?,8-,9?,10?,11-,12?,13?,16-/m1/s1 RRCFLRBBBFZLSB-MPMHWICOSA-N logp -1.99 ALOGPS logs -1.58 ALOGPS solubility 1.12e+01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 8.12 ChemAxon pka_strongest_basic 7.19 ChemAxon iupac 4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol ChemAxon average_mass 425.3932 ChemAxon mono_mass 425.154662737 ChemAxon smiles [H]C12OC1([H])C([H])(NCC1=CN(C3=C1C(O)=NC(=N)N3)[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O)C([H])(O)C2([H])O ChemAxon formula C17H23N5O8 ChemAxon inchi InChI=1S/C17H23N5O8/c18-17-20-14-6(15(28)21-17)4(1-19-7-9(25)10(26)13-12(7)30-13)2-22(14)16-11(27)8(24)5(3-23)29-16/h2,5,7-13,16,19,23-27H,1,3H2,(H3,18,20,21,28)/t5-,7?,8-,9?,10?,11-,12?,13?,16-/m1/s1 ChemAxon inchikey RRCFLRBBBFZLSB-MPMHWICOSA-N ChemAxon polar_surface_area 208.34 ChemAxon refractivity 108.67 ChemAxon polarizability 41.18 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 12 ChemAxon donor_count 9 ChemAxon physiological_charge 2 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 1083323 Specdb::NmrOneD 332558 Specdb::NmrOneD 332559 Specdb::NmrOneD 332560 Specdb::NmrOneD 332561 Specdb::NmrOneD 332562 Specdb::NmrOneD 332563 Specdb::NmrOneD 332564 Specdb::NmrOneD 332565 Specdb::NmrOneD 332566 Specdb::NmrOneD 332567 Specdb::NmrOneD 332568 Specdb::NmrOneD 332569 Specdb::NmrOneD 332570 Specdb::NmrOneD 332571 Specdb::NmrOneD 332572 Specdb::NmrOneD 332573 Specdb::NmrOneD 332574 Specdb::NmrOneD 332575 Specdb::NmrOneD 332576 Specdb::NmrOneD 332577 Specdb::MsMs 27971 Specdb::MsMs 27972 Specdb::MsMs 27973 Specdb::MsMs 34529 Specdb::MsMs 34530 Specdb::MsMs 34531 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 7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine > Hydrogen ion + L-Methionine + Adenine + epoxyqueuosine PW_R005185