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Record Information
Version	2.0
Creation Date	2012-05-31 13:01:01 -0600
Update Date	2015-06-03 15:53:35 -0600
Secondary Accession Numbers	ECMDB00751
Identification
Name:	L-Threo-2-pentulose
Description	L-Threo-2-pentulose, also called L-xylulose, is a ketopentose - a monosaccharide containing five carbon atoms, and including a ketone functional group. It has chemical formula C5H10O5. In nature it occurs in the L- and D- isomers. (Wikipedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb1a0655c> Close
Synonyms:	L-Xylulose
Chemical Formula:	C5H10O5
Weight:	Average: 150.1299 Monoisotopic: 150.05282343
InChI Key:	ZAQJHHRNXZUBTE-WVZVXSGGSA-N
InChI:	InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1
CAS number:	527-50-4
IUPAC Name:	(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one
Traditional IUPAC Name:	xylulose
SMILES:	OC[C@H](O)[C@@H](O)C(=O)CO
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 ketones Acyloins Alpha-hydroxy ketones Secondary alcohols Polyols Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Pentose monosaccharide Beta-hydroxy ketone Acyloin Alpha-hydroxy ketone Secondary alcohol Ketone Polyol Organic oxide Hydrocarbon derivative Primary alcohol Carbonyl group Alcohol Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	xylulose (CHEBI:17399 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 678 g/L ALOGPS logP -2.2 ALOGPS logP -2.6 ChemAxon logS 0.65 ALOGPS pKa (Strongest Acidic) 10.57 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 31.6 m³·mol⁻¹ ChemAxon Polarizability 13.5 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:	Adenosine triphosphate + L-Threo-2-pentulose <> ADP + Hydrogen ion + L-Xylulose 5-phosphate L-Lyxose > L-Threo-2-pentulose Adenosine triphosphate + L-Threo-2-pentulose <> ADP + L-Xylulose 5-phosphate Adenosine triphosphate + L-Threo-2-pentulose <> ADP + L-Xylulose 1-phosphate Adenosine triphosphate + L-Threo-2-pentulose > ADP + L-Xylulose 5-phosphate L-Threo-2-pentulose + Adenosine triphosphate + L-Threo-2-pentulose > Xylulose 5-phosphate + Adenosine diphosphate + Xylulose 5-phosphate + ADP β-D-xylopyranose <> L-Threo-2-pentulose L-Threo-2-pentulose + Adenosine triphosphate > Xylulose 5-phosphate + ADP + Hydrogen ion L-Threo-2-pentulose + Adenosine triphosphate > L-Xylulose 5-phosphate + ADP + Hydrogen ion β-L-lyxopyranose <> L-Threo-2-pentulose
SMPDB Pathways:	L-lyxose Degradation PW002100 Xylose Degradation I PW002105
KEGG Pathways:	Ascorbate and aldarate metabolism ec00053 Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03di-9000000000-5e0dfc74544a16cb6a2b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-00g3-9127300000-b6aed5448276d0184bc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-2900000000-3e1ebc07944b3d190ec8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-9300000000-bca65135a1359f774229 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-08fv-9000000000-71ba0bd1388ac4ba066d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000j-9400000000-a8afb4fe5a51e50f0c41 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052r-9200000000-bbc5e84222a57470dc89 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-ce9ee9286404da2668c5 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:	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 Oka H, Suzuki S, Suzuki H, Oda T: Increased urinary excretion of L-xylulose in patients with liver cirrhosis. Clin Chim Acta. 1976 Mar 1;67(2):131-6. Pubmed: 1248150 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:	Ashwell, Gilbert; Kanfer, Julian; Burns, J. J. Mechanism of L-xylulose formation by kidney enzymes. Journal of Biological Chemistry (1959), 234 472-5.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17399 HMDB ID HMDB00751 Pubchem Compound ID 439205 Kegg ID C00312 ChemSpider ID 20892 Wikipedia ID Xylulose BioCyc ID Not Available

Enzymes

Transporters