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Record Information
Version	2.0
Creation Date	2012-05-31 14:37:05 -0600
Update Date	2015-06-03 17:19:42 -0600
Secondary Accession Numbers	ECMDB20282
Identification
Name:	L-Ribose
Description	Ribose is an organic compound that occurs widely in nature. It is an aldopentose, a monosaccharide containing five carbon atoms that in its acyclic form has an aldehyde functional group at one end. Typically, ribose exists in the cyclic form. It comprises the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA, by the removal of one hydroxy group. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism. Ribose exists in two enantiomeric forms, primarily as D-ribose. L-ribose is the synthetic mirror image of D-ribose. (Wikipedia) In E. coli, L-ribose can act as an competitive inhibitor of glucose dehydrogenase. (EcoCyc)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa0012e94> Close
Synonyms:	(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal Aldehydo-L-ribo-pentose Aldehydo-L-ribose Arabinose
Chemical Formula:	C5H10O5
Weight:	Average: 150.1299 Monoisotopic: 150.05282343
InChI Key:	PYMYPHUHKUWMLA-MROZADKFSA-N
InChI:	InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m1/s1
CAS number:	24259-59-4
IUPAC Name:	(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal
Traditional IUPAC Name:	L-ribose
SMILES:	[H][C@](O)(CO)[C@]([H])(O)[C@]([H])(O)C=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	Beta-hydroxy aldehydes Alpha-hydroxyaldehydes Secondary alcohols Polyols Short-chain aldehydes Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Pentose monosaccharide Beta-hydroxy aldehyde Alpha-hydroxyaldehyde Secondary alcohol Polyol Organic oxide Hydrocarbon derivative Short-chain aldehyde Primary alcohol Carbonyl group Aldehyde Alcohol Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	aldehydo-ribose (CHEBI:47015 ) L-ribose (CHEBI:47015 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	99 °C, 372 K, 210 °F
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 380 g/L ALOGPS logP -2.3 ALOGPS logP -2.9 ChemAxon logS 0.4 ALOGPS pKa (Strongest Acidic) 11.87 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 97.99 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 31.38 m³·mol⁻¹ ChemAxon Polarizability 13.38 ų ChemAxon Number of Rings 0 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:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-2900000000-d4b4d16fe2bdea6dccd0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-9300000000-be87d057e4e6e95de7e5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-08fv-9000000000-9a3060e3aacc77a20cca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000j-9400000000-dbd7597b23c261cf03b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06ri-9200000000-bf3ea96e46d76c202a29 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-6b0fd940d309cdea3a46 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:	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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 46997 HMDB ID Not Available Pubchem Compound ID 90428 Kegg ID Not Available ChemSpider ID 81643 Wikipedia ID Ribose BioCyc ID CPD-6001 EcoCyc ID CPD-6001

Enzymes

Transporters