2.02012-05-31 14:32:16 -06002015-06-03 17:19:30 -0600ECMDB20190M2MDB001036S-Ribosyl-L-homocysteineS-ribosyl-L-homocysteine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). AI-2 is spontaneously derived from 4,5-dihydroxy-2,3-pentanedione that, along with homocysteine, is produced by cleavage of S-adenosylhomocysteine (SAH) and S-ribosylhomocysteine by the Pfs and LuxS enzymes. (PMID 16885435)<i>S</i>-(5-deoxy-D-ribos-5-yl)-L-homocysteineRHCRibHomoCysRibose-5-<i>S</i>-homocysteineRibose-5-S-homocysteineS-(5-Deoxy-D-ribos-5-yl)-L-homocysteineS-D-Ribosyl-L-homocysteineS-Ribosyl-L-homocysteineS-RibosylhomocysteineC9H17NO6S267.299267.077657971(2S)-2-amino-4-({[(2S,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acidribose-5-S-homocysteine15912-98-8[H][C@](N)(CCSC[C@@]1([H])OC([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=OInChI=1S/C9H17NO6S/c10-4(8(13)14)1-2-17-3-5-6(11)7(12)9(15)16-5/h4-7,9,11-12,15H,1-3,10H2,(H,13,14)/t4-,5+,6+,7+,9?/m0/s1IQFWYNFDWRYSRA-BLELIYKESA-NCytosollogp-2.58logs-0.81solubility4.10e+01 g/llogp-4.2pka_strongest_acidic1.8pka_strongest_basic9.5iupac(2S)-2-amino-4-({[(2S,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acidaverage_mass267.299mono_mass267.077657971smiles[H][C@](N)(CCSC[C@@]1([H])OC([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=OformulaC9H17NO6SinchiInChI=1S/C9H17NO6S/c10-4(8(13)14)1-2-17-3-5-6(11)7(12)9(15)16-5/h4-7,9,11-12,15H,1-3,10H2,(H,13,14)/t4-,5+,6+,7+,9?/m0/s1inchikeyIQFWYNFDWRYSRA-BLELIYKESA-Npolar_surface_area133.24refractivity59.49polarizability26.51rotatable_bond_count6acceptor_count7donor_count5physiological_charge0formal_charge0Cysteine and methionine metabolismec00270Metabolic pathwayseco01100<i>S</i>-adenosyl-L-methionine cycle IPWY-6151autoinducer AI-2 biosynthesis IPWY-6153Specdb::CMs1085089Specdb::EiMs2065Specdb::NmrOneD331142Specdb::NmrOneD331143Specdb::NmrOneD331144Specdb::NmrOneD331145Specdb::NmrOneD331146Specdb::NmrOneD331147Specdb::NmrOneD331148Specdb::NmrOneD331149Specdb::NmrOneD331150Specdb::NmrOneD331151Specdb::NmrOneD331152Specdb::NmrOneD331153Specdb::NmrOneD331154Specdb::NmrOneD331155Specdb::NmrOneD331156Specdb::NmrOneD331157Specdb::NmrOneD331158Specdb::NmrOneD331159Specdb::NmrOneD331160Specdb::NmrOneD331161Specdb::MsMs24581Specdb::MsMs24582Specdb::MsMs24583Specdb::MsMs31139Specdb::MsMs31140Specdb::MsMs31141440041389052C03539CPD-564Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Walters, M., Sircili, M. P., Sperandio, V. (2006). "AI-3 synthesis is not dependent on luxS in Escherichia coli." J Bacteriol 188:5668-5681.168854355'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseP0AF12MTNN_ECOLImtnNhttp://ecmdb.ca/proteins/P0AF12.xmlS-ribosylhomocysteine lyaseP45578LUXS_ECOLIluxShttp://ecmdb.ca/proteins/P45578.xmlS-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteineR00194ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXNS-Ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + L-HomocysteineRIBOSYLHOMOCYSTEINASE-RXNS-Ribosyl-L-homocysteine <> (4S)-4,5-Dihydroxypentan-2,3-dione + L-HomocysteineR01291S-Ribosyl-L-homocysteine + Adenine < S-Adenosylhomocysteine + WaterR00194ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXNS-Ribosyl-L-homocysteine > L-Homocysteine + (4S)-4,5-Dihydroxypentan-2,3-dioneS-Adenosylhomocysteine + Water > S-Ribosyl-L-homocysteine + Adenine