1.0 2011-09-21 00:27:34 UTC 2025-11-19 02:43:41 UTC FDB023288 N6-Methyladenosine N6-Methyladenosine is a methylated adenine residue. N6-Methyladenosine is an endogenous urinary nucleoside product of the degradation of transfer ribonucleic acid (tRNA); urinary nucleosides are biological markers for patients with colorectal cancer. tRNA has been shown to be excreted in abnormal amounts in the urine of cancer patients. tRNA from neoplastic tissue had a much more rapid turnover rate than the tRNA from the corresponding normal tissue. Evidence indicates that methylation of tRNA occurs only after synthesis of the intact macromolecule. Because there are no specific enzyme systems to incorporate the modified nucleosides into the macromolecular nucleic acid, these nucleosides once released in the process of tRNA turnover cannot be reutilized, nor are they further degraded, but are excreted in urine. (PMID: 15991285, 3506820) [HMDB] (2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3,4-diol 6-Methyladenosine 6-methylamino-9-beta-D-ribofuranosyl-Purine 6-methylamino-9-beta-delta-ribofuranosyl-Purine 6-Methylaminopurine D-riboside 6-Methylaminopurine ribonucleoside 6-Methylaminopurine riboside 6-Methylaminopurinosine m6a N-methyladenosine N(6)-Methyladenosine N(6)-Monomethyladenosine C11H15N5O4 281.2679 281.112403993 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolane-3,4-diol N6-methyladenosine 1867-73-8 CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O InChI=1S/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11-/m1/s1 VQAYFKKCNSOZKM-IOSLPCCCSA-N belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Purine nucleosides Organic compounds Nucleosides, nucleotides, and analogues Purine nucleosides Aromatic heteropolycyclic compounds 6-alkylaminopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams N-substituted imidazoles Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Secondary alcohols Secondary alkylarylamines Tetrahydrofurans 6-alkylaminopurine 6-aminopurine Alcohol Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monosaccharide N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Purine Purine nucleoside Pyrimidine Secondary alcohol Secondary aliphatic/aromatic amine Secondary amine Tetrahydrofuran methyladenosine Solid logp -0.64 ALOGPS logs -1.46 ALOGPS solubility 9.77e+00 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 12.45 ChemAxon pka_strongest_basic 4.89 ChemAxon iupac (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolane-3,4-diol ChemAxon average_mass 281.2679 ChemAxon mono_mass 281.112403993 ChemAxon smiles CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ChemAxon formula C11H15N5O4 ChemAxon inchi InChI=1S/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11-/m1/s1 ChemAxon inchikey VQAYFKKCNSOZKM-IOSLPCCCSA-N ChemAxon polar_surface_area 125.55 ChemAxon refractivity 68.69 ChemAxon polarizability 27.59 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17796 Specdb::CMs 38693 Specdb::CMs 147296 Specdb::MsMs 305404 Specdb::MsMs 305405 Specdb::MsMs 305406 Specdb::MsMs 348811 Specdb::MsMs 348812 Specdb::MsMs 348813 Specdb::MsMs 2248846 Specdb::MsMs 2249523 Specdb::MsMs 2250847 Specdb::MsMs 2251574 Specdb::MsMs 2777957 Specdb::MsMs 2777958 Specdb::MsMs 2777959 Specdb::MsMs 2901444 Specdb::MsMs 2901445 Specdb::MsMs 2901446 Specdb::NmrOneD 10722 Specdb::NmrOneD 10723 Specdb::NmrOneD 10724 Specdb::NmrOneD 10725 Specdb::NmrOneD 10726 Specdb::NmrOneD 10727 Specdb::NmrOneD 10728 Specdb::NmrOneD 10729 Specdb::NmrOneD 10730 Specdb::NmrOneD 10731 Specdb::NmrOneD 10732 Specdb::NmrOneD 10733 Specdb::NmrOneD 10734 Specdb::NmrOneD 10735 Specdb::NmrOneD 10736 Specdb::NmrOneD 10737 Specdb::NmrOneD 10738 Specdb::NmrOneD 10739 Specdb::NmrOneD 10740 Specdb::NmrOneD 10741 HMDB04044 #<Reference:0x000055ce329dd3b0> #<Reference:0x000055ce329dcfa0> 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