2.0 2012-05-31 14:32:16 -0600 2015-06-03 17:19:30 -0600 ECMDB20190 M2MDB001036 S-Ribosyl-L-homocysteine S-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) S-(5-deoxy-D-ribos-5-yl)-L-homocysteine RHC RibHomoCys Ribose-5-S-homocysteine Ribose-5-S-homocysteine S-(5-Deoxy-D-ribos-5-yl)-L-homocysteine S-D-Ribosyl-L-homocysteine S-Ribosyl-L-homocysteine S-Ribosylhomocysteine C9H17NO6S 267.299 267.077657971 (2S)-2-amino-4-({[(2S,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid ribose-5-S-homocysteine 15912-98-8 [H][C@](N)(CCSC[C@@]1([H])OC([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O InChI=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/s1 IQFWYNFDWRYSRA-BLELIYKESA-N Cytosol logp -2.58 ALOGPS logs -0.81 ALOGPS solubility 4.10e+01 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.8 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac (2S)-2-amino-4-({[(2S,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid ChemAxon average_mass 267.299 ChemAxon mono_mass 267.077657971 ChemAxon smiles [H][C@](N)(CCSC[C@@]1([H])OC([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O ChemAxon formula C9H17NO6S ChemAxon inchi InChI=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/s1 ChemAxon inchikey IQFWYNFDWRYSRA-BLELIYKESA-N ChemAxon polar_surface_area 133.24 ChemAxon refractivity 59.49 ChemAxon polarizability 26.51 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 S-adenosyl-L-methionine cycle I PWY-6151 autoinducer AI-2 biosynthesis I PWY-6153 Specdb::CMs 1085089 Specdb::EiMs 2065 Specdb::NmrOneD 331142 Specdb::NmrOneD 331143 Specdb::NmrOneD 331144 Specdb::NmrOneD 331145 Specdb::NmrOneD 331146 Specdb::NmrOneD 331147 Specdb::NmrOneD 331148 Specdb::NmrOneD 331149 Specdb::NmrOneD 331150 Specdb::NmrOneD 331151 Specdb::NmrOneD 331152 Specdb::NmrOneD 331153 Specdb::NmrOneD 331154 Specdb::NmrOneD 331155 Specdb::NmrOneD 331156 Specdb::NmrOneD 331157 Specdb::NmrOneD 331158 Specdb::NmrOneD 331159 Specdb::NmrOneD 331160 Specdb::NmrOneD 331161 Specdb::MsMs 24581 Specdb::MsMs 24582 Specdb::MsMs 24583 Specdb::MsMs 31139 Specdb::MsMs 31140 Specdb::MsMs 31141 440041 389052 C03539 CPD-564 Keseler, 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. 21097882 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Walters, M., Sircili, M. P., Sperandio, V. (2006). "AI-3 synthesis is not dependent on luxS in Escherichia coli." J Bacteriol 188:5668-5681. 16885435 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI mtnN http://ecmdb.ca/proteins/P0AF12.xml S-ribosylhomocysteine lyase P45578 LUXS_ECOLI luxS http://ecmdb.ca/proteins/P45578.xml S-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteine R00194 ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXN S-Ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + L-Homocysteine RIBOSYLHOMOCYSTEINASE-RXN S-Ribosyl-L-homocysteine <> (4S)-4,5-Dihydroxypentan-2,3-dione + L-Homocysteine R01291 S-Ribosyl-L-homocysteine + Adenine < S-Adenosylhomocysteine + Water R00194 ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXN S-Ribosyl-L-homocysteine > L-Homocysteine + (4S)-4,5-Dihydroxypentan-2,3-dione S-Adenosylhomocysteine + Water > S-Ribosyl-L-homocysteine + Adenine