1.0 2011-09-21 01:37:42 UTC 2015-07-21 06:59:22 UTC FDB028309 Queuosine Queuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes. Originally identified in E. coli, queuosine was found to occupy the first anticodon position of tRNAs for histidine, aspartic acid, asparagine and tyrosine. The first anticodon position pairs with the third "wobble" position in codons, and queuosine improves accuracy of translation. Synthesis of queuosine begins with GTP. In bacteria, two classes of riboswitch are known to regulate genes that are involved in the synthesis or transport of pre-queuosine1, a precursor to queuosine: PreQ1-I riboswitches and PreQ1-II riboswitches. from wikipedia [HMDB] (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (imidazol-4-yl)acetaldehyde C17H23N5O7 409.3938 409.159748115 2-amino-7-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one 2-amino-7-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H-pyrrolo[2,3-d]pyrimidin-4-one 57072-36-3 NC1=NC(=O)C2=C(N1)N(C=C2CN[C@H]1C=C[C@H](O)[C@@H]1O)C1O[C@H](CO)[C@@H](O)[C@H]1O InChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16?/m0/s1 QQXQGKSPIMGUIZ-FSIZVHFJSA-N belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7. Pyrrolopyrimidine nucleosides and nucleotides Organic compounds Nucleosides, nucleotides, and analogues Pyrrolopyrimidine nucleosides and nucleotides Aromatic heteropolycyclic compounds Aminopyrimidines and derivatives Aralkylamines Azacyclic compounds Dialkylamines Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Primary amines Pyrimidones Pyrrolo[2,3-d]pyrimidines Secondary alcohols Substituted pyrroles Tetrahydrofurans Vinylogous amides Alcohol Amine Aminopyrimidine Aralkylamine Aromatic heteropolycyclic compound Azacycle Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Monosaccharide N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Primary amine Pyrimidine Pyrimidone Pyrrole Pyrrolo[2,3-d]pyrimidine Pyrrolopyrimidine Pyrrolopyrimidine ribonucleoside Secondary alcohol Secondary aliphatic amine Secondary amine Substituted pyrrole Tetrahydrofuran Vinylogous amide Solid logp -1.85 ALOGPS logs -1.71 ALOGPS solubility 7.96e+00 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 9.06 ChemAxon pka_strongest_basic 7.21 ChemAxon iupac 2-amino-7-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one ChemAxon average_mass 409.3938 ChemAxon mono_mass 409.159748115 ChemAxon smiles NC1=NC(=O)C2=C(N1)N(C=C2CN[C@H]1C=C[C@H](O)[C@@H]1O)C1O[C@H](CO)[C@@H](O)[C@H]1O ChemAxon formula C17H23N5O7 ChemAxon inchi InChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16?/m0/s1 ChemAxon inchikey QQXQGKSPIMGUIZ-FSIZVHFJSA-N ChemAxon polar_surface_area 194.82 ChemAxon refractivity 99.56 ChemAxon polarizability 40.65 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26405 Specdb::CMs 39715 Specdb::CMs 132150 Specdb::CMs 139884 Specdb::MsMs 324535 Specdb::MsMs 324536 Specdb::MsMs 324537 Specdb::MsMs 372967 Specdb::MsMs 372968 Specdb::MsMs 372969 Specdb::MsMs 2463159 Specdb::MsMs 2463160 Specdb::MsMs 2463161 Specdb::MsMs 2499710 Specdb::MsMs 2499711 Specdb::MsMs 2499712 Specdb::NmrOneD 93312 Specdb::NmrOneD 93313 Specdb::NmrOneD 93314 Specdb::NmrOneD 93315 Specdb::NmrOneD 93316 Specdb::NmrOneD 93317 Specdb::NmrOneD 93318 Specdb::NmrOneD 93319 Specdb::NmrOneD 93320 Specdb::NmrOneD 93321 Specdb::NmrOneD 93322 Specdb::NmrOneD 93323 Specdb::NmrOneD 93324 Specdb::NmrOneD 93325 Specdb::NmrOneD 93326 Specdb::NmrOneD 93327 Specdb::NmrOneD 93328 Specdb::NmrOneD 93329 Specdb::NmrOneD 93330 Specdb::NmrOneD 93331 HMDB11596 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823