1.0 2011-09-21 00:17:29 UTC 2015-07-21 06:57:17 UTC FDB022654 Queuine Queuine is a highly modified derivative of guanine found in the first position of the anticodon of the transfer RNAs for asp, asn, his and tyr. The original transcripts of these tRNAs contain guanine in this position. All organisms with the exception of yeast and mycoplasma contain queuine. Bacteria synthesize queuine but it cannot be synthesized by higher mammals. Significant amounts of free queuine are present in common plant and animal food products. (PMID 9016755) [HMDB] 2-amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo(2,3-d)pyrimidin-4-one 7-(3,4-trans-4,5-cis-dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine Base Q Queuine C12H15N5O3 277.2792 277.117489371 5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one 5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,3H,7H-pyrrolo[2,3-d]pyrimidin-4-one 72496-59-4 O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1 WYROLENTHWJFLR-BHNWBGBOSA-N belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions. Pyrrolo[2,3-d]pyrimidines Organic compounds Organoheterocyclic compounds Pyrrolopyrimidines Pyrrolo[2,3-d]pyrimidines Aromatic heteropolycyclic compounds 1,2-diols Aminopyrimidines and derivatives Aralkylamines Azacyclic compounds Dialkylamines Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines Pyrimidones Secondary alcohols Substituted pyrroles Vinylogous amides 1,2-diol Alcohol Amine Aminopyrimidine Aralkylamine Aromatic heteropolycyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Pyrimidine Pyrimidone Pyrrole Pyrrolo[2,3-d]pyrimidine Secondary alcohol Secondary aliphatic amine Secondary amine Substituted pyrrole Vinylogous amide Solid logp -1.10 ALOGPS logs -2.95 ALOGPS solubility 3.08e-01 g/l ALOGPS logp -0.71 ChemAxon pka_strongest_acidic 11.11 ChemAxon pka_strongest_basic 7.43 ChemAxon iupac 5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one ChemAxon average_mass 277.2792 ChemAxon mono_mass 277.117489371 ChemAxon smiles O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O ChemAxon formula C12H15N5O3 ChemAxon inchi InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1 ChemAxon inchikey WYROLENTHWJFLR-BHNWBGBOSA-N ChemAxon polar_surface_area 133.26 ChemAxon refractivity 83.45 ChemAxon polarizability 27.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 7 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19777 Specdb::CMs 38096 Specdb::CMs 136405 Specdb::CMs 144139 Specdb::MsMs 310033 Specdb::MsMs 310034 Specdb::MsMs 310035 Specdb::MsMs 354607 Specdb::MsMs 354608 Specdb::MsMs 354609 Specdb::MsMs 2831530 Specdb::MsMs 2831531 Specdb::MsMs 2831532 Specdb::MsMs 2847590 Specdb::MsMs 2847591 Specdb::MsMs 2847592 Specdb::NmrOneD 9442 Specdb::NmrOneD 9443 Specdb::NmrOneD 9444 Specdb::NmrOneD 9445 Specdb::NmrOneD 9446 Specdb::NmrOneD 9447 Specdb::NmrOneD 9448 Specdb::NmrOneD 9449 Specdb::NmrOneD 9450 Specdb::NmrOneD 9451 Specdb::NmrOneD 9452 Specdb::NmrOneD 9453 Specdb::NmrOneD 9454 Specdb::NmrOneD 9455 Specdb::NmrOneD 9456 Specdb::NmrOneD 9457 Specdb::NmrOneD 9458 Specdb::NmrOneD 9459 Specdb::NmrOneD 9460 Specdb::NmrOneD 9461 HMDB01495 17433 #<Reference:0x000055ce318b3300> #<Reference:0x000055ce318b3148> Queuine tRNA-ribosyltransferase subunit QTRTD1 Q9H974 QTRTD1