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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:19 -0600
Update Date	2015-09-14 16:46:11 -0600
Secondary Accession Numbers	ECMDB24231
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab110cf0> Close
Synonyms:	Not Available
Chemical Formula:	C9H14NO6S
Weight:	Average: 264.27 Monoisotopic: 264.054183349
InChI Key:	QUDMRZABJLFLCP-UHFFFAOYSA-M
InChI:	InChI=1S/C9H15NO6S/c10-4(8(13)14)1-2-17-3-5-6(11)7(12)9(15)16-5/h4-7,9,11-12,15H,1-3H2,(H,13,14)/q+1/p-1
CAS number:	Not Available
IUPAC Name:	(1-carboxylato-3-{[(3,4,5-trihydroxyoxolan-2-yl)methyl]sulfanyl}propyl)azaniumyl
Traditional IUPAC Name:	(1-carboxylato-3-{[(3,4,5-trihydroxyoxolan-2-yl)methyl]sulfanyl}propyl)ammonio
SMILES:	[N+]C(CCSCC1OC(O)C(O)C1O)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	Alpha amino acids and derivatives Thia fatty acids Heterocyclic fatty acids Hydroxy fatty acids Tetrahydrofurans 1,2-diols Secondary alcohols Carboxylic acid salts Hemiacetals Sulfenyl compounds Oxacyclic compounds Carboxylic acids Dialkylthioethers Monocarboxylic acids and derivatives Organonitrogen compounds Organopnictogen compounds Organic zwitterions Hydrocarbon derivatives Organic salts Carbonyl compounds Organic oxides
Substituents	Alpha-amino acid or derivatives Pentose monosaccharide Heterocyclic fatty acid Hydroxy fatty acid Thia fatty acid Fatty acyl Fatty acid Tetrahydrofuran 1,2-diol Carboxylic acid salt Hemiacetal Secondary alcohol Dialkylthioether Sulfenyl compound Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Polyol Oxacycle Organoheterocyclic compound Thioether Organic oxide Organopnictogen compound Carbonyl group Organonitrogen compound Organosulfur compound Hydrocarbon derivative Organic zwitterion Organic nitrogen compound Alcohol Organic salt Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 26.9 g/L ALOGPS logP -2.1 ALOGPS logP -2.9 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.63 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 133.11 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 68.8 m³·mol⁻¹ ChemAxon Polarizability 25.52 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 S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine > Homocysteine + autoinducer 2 + Homocysteine + autoinducer 2 S-ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + Homocysteine
SMPDB Pathways:	Quorum Sensing PW000836 S-adenosyl-L-methionine cycle PW002080
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01b9-1590000000-42b048d2c23ca96f5908 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0gb9-2930000000-4919a12118e6bf75521f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03dr-9400000000-1a13f170188e308b164a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0292-2690000000-68581f80437bb7da635e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00kb-3960000000-21c3f9415cf6a4b74a29 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0aos-9700000000-dd64ac19f6fcc0bb8d5c View in MoNA 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes