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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:16 -0600
Update Date	2015-06-03 17:19:30 -0600
Secondary Accession Numbers	ECMDB20190
Identification
Name:	S-Ribosyl-L-homocysteine
Description	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)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa0d575f0> Close
Synonyms:	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
Chemical Formula:	C9H17NO6S
Weight:	Average: 267.299 Monoisotopic: 267.077657971
InChI Key:	IQFWYNFDWRYSRA-BLELIYKESA-N
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
CAS number:	15912-98-8
IUPAC Name:	(2S)-2-amino-4-({[(2S,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
Traditional IUPAC Name:	ribose-5-S-homocysteine
SMILES:	[H][C@](N)(CCSC[C@@]1([H])OC([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Pentoses
Alternative Parents	L-alpha-amino acids Thia fatty acids Heterocyclic fatty acids Hydroxy fatty acids Tetrahydrofurans 1,2-diols Secondary alcohols Amino acids Hemiacetals Sulfenyl compounds Oxacyclic compounds Carboxylic acids Dialkylthioethers Monocarboxylic acids and derivatives Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Monoalkylamines
Substituents	Alpha-amino acid Alpha-amino acid or derivatives L-alpha-amino acid Pentose monosaccharide Heterocyclic fatty acid Hydroxy fatty acid Thia fatty acid Fatty acyl Fatty acid Tetrahydrofuran 1,2-diol Amino acid Amino acid or derivatives Hemiacetal Secondary alcohol Carboxylic acid derivative Carboxylic acid Oxacycle Organoheterocyclic compound Dialkylthioether Monocarboxylic acid or derivatives Sulfenyl compound Polyol Thioether Organopnictogen compound Alcohol Organic oxide Primary aliphatic amine Amine Organonitrogen compound Organosulfur compound Hydrocarbon derivative Carbonyl group Primary amine Organic nitrogen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	homocysteines (CHEBI:17575 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 41 g/L ALOGPS logP -2.6 ALOGPS logP -4.2 ChemAxon logS -0.81 ALOGPS pKa (Strongest Acidic) 1.8 ChemAxon pKa (Strongest Basic) 9.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 133.24 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 59.49 m³·mol⁻¹ ChemAxon Polarizability 26.51 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	S-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteine S-Ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + L-Homocysteine S-Ribosyl-L-homocysteine <> (4S)-4,5-Dihydroxypentan-2,3-dione + L-Homocysteine S-Ribosyl-L-homocysteine + Adenine < S-Adenosylhomocysteine + Water S-Ribosyl-L-homocysteine > L-Homocysteine + (4S)-4,5-Dihydroxypentan-2,3-dione S-Adenosylhomocysteine + Water > S-Ribosyl-L-homocysteine + Adenine
SMPDB Pathways:	Not Available
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100
EcoCyc Pathways:	S-adenosyl-L-methionine cycle I PWY-6151 autoinducer AI-2 biosynthesis I PWY-6153
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0v4i-1490000000-a563ced55f82e8070620 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0awl-6940000000-6f3b4a6abff4c6480a68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-9300000000-ec0c015f9099ed6a02a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-1980000000-d38c80c34d9b3ddb390f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00lr-2910000000-6a40a387796ae281b565 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a59-9600000000-eb2fe9f3863fefa956e0 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510 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. Pubmed: 21097882 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. Pubmed: 17765195 Walters, M., Sircili, M. P., Sperandio, V. (2006). "AI-3 synthesis is not dependent on luxS in Escherichia coli." J Bacteriol 188:5668-5681. Pubmed: 16885435 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. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17575 HMDB ID Not Available Pubchem Compound ID 440041 Kegg ID C03539 ChemSpider ID 389052 Wikipedia ID Not Available BioCyc ID CPD-564 EcoCyc ID CPD-564

Enzymes