Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 10:28:15 -0600
Update Date	2015-09-13 12:56:08 -0600
Secondary Accession Numbers	ECMDB00654
Identification
Name:	D-Xylulose
Description	D-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337, Mol Genet Metab. 2004 Jul;82(3):231-7.)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb4dafe30> Close
Synonyms:	D-Threo-Pentulose D-Xylulose Xylulose
Chemical Formula:	C5H10O5
Weight:	Average: 150.1299 Monoisotopic: 150.05282343
InChI Key:	ZAQJHHRNXZUBTE-WUJLRWPWSA-N
InChI:	InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1
CAS number:	551-84-8
IUPAC Name:	(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one
Traditional IUPAC Name:	D-xylulose
SMILES:	[H][C@@](O)(CO)[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:17140 )
Physical Properties
State:	Liquid
Charge:	0
Melting point:	15 °C
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 13.53 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 + D-Xylulose <> ADP + Hydrogen ion + Xylulose 5-phosphate D-Xylose <> D-Xylulose Adenosine triphosphate + D-Xylulose <> ADP + Xylulose 5-phosphate D-xylose <> D-Xylulose D-Xylulose + Adenosine triphosphate > Hydrogen ion + Xylulose 5-phosphate + ADP D-Xylose > D-Xylulose Adenosine triphosphate + D-Xylulose > ADP + Xylulose 5-phosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Fructose and mannose metabolism ec00051 Metabolic pathways eco01100 Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:	xylose degradation I XYLCAT-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-00kb-0930000000-c3a525ee2ad524114f0d View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03di-9100000000-1304cf35b8860cd7a456 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positive splash10-00g3-9127300000-b6aed5448276d0184bc2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-014r-4900000000-0a4d51584b79dc230edb View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-000i-9000000000-2131da3ca52caffed55f View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-014i-9000000000-305f431957b24a5b888a 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-9300000000-9be7fcf2c9ec6f8829c7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-08fv-9000000000-931753afec5aa068bca8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000j-9400000000-1c39b6f316e1745d355c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06ri-9100000000-095c1d8c10895109ecb1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-5ea417513158cb617f30 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Huck, J. H., Roos, B., Jakobs, C., van der Knaap, M. S., Verhoeven, N. M. (2004). "Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism." Mol Genet Metab 82:231-237. Pubmed: 15234337 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 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:	Takeuchi, Sonoko; Tonouchi, Naoto; Yokozeki, Kenzo. Production of xylitol or D-xylulose by fermentation of glucose with Gluconobacter, Acetobacter, and Frateuria. Eur. Pat. Appl. (2000), 10 pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 17140 HMDB ID HMDB01644 Pubchem Compound ID 619 Kegg ID C00310 ChemSpider ID 4451524 Wikipedia Xylulose BioCyc ID D-XYLULOSE EcoCyc ID D-XYLULOSE Ligand Expo XUL

Enzymes

Transporters