Record Information
Version2.0
Creation Date2012-05-31 13:01:01 -0600
Update Date2015-06-03 15:53:35 -0600
Secondary Accession Numbers
  • ECMDB00751
Identification
Name:L-Threo-2-pentulose
DescriptionL-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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility678 g/LALOGPS
logP-2.2ALOGPS
logP-2.6ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)10.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.6 m³·mol⁻¹ChemAxon
Polarizability13.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
L-lyxose DegradationPW002100 ThumbThumb?image type=greyscaleThumb?image type=simple
Xylose Degradation IPW002105 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Ascorbate and aldarate metabolism ec00053
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-5e0dfc74544a16cb6a2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00g3-9127300000-b6aed5448276d0184bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-3e1ebc07944b3d190ec8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-bca65135a1359f774229View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-71ba0bd1388ac4ba066dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-a8afb4fe5a51e50f0c41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9200000000-bbc5e84222a57470dc89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ce9ee9286404da2668c5View in MoNA
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
External Links:
ResourceLink
CHEBI ID17399
HMDB IDHMDB00751
Pubchem Compound ID439205
Kegg IDC00312
ChemSpider ID20892
Wikipedia IDXylulose
BioCyc IDNot Available

Enzymes

General function:
Involved in xylose isomerase activity
Specific function:
D-xylose = D-xylulose
Gene Name:
xylA
Uniprot ID:
P00944
Molecular weight:
49742
Reactions
D-xylose = D-xylulose.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + L(or D)-ribulose = ADP + L(or D)- ribulose 5-phosphate
Gene Name:
araB
Uniprot ID:
P08204
Molecular weight:
61089
Reactions
ATP + L(or D)-ribulose = ADP + L(or D)-ribulose 5-phosphate.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + D-xylulose = ADP + D-xylulose 5- phosphate
Gene Name:
xylB
Uniprot ID:
P09099
Molecular weight:
52618
Reactions
ATP + D-xylulose = ADP + D-xylulose 5-phosphate.
General function:
Involved in L-rhamnose isomerase activity
Specific function:
L-rhamnose = L-rhamnulose
Gene Name:
rhaA
Uniprot ID:
P32170
Molecular weight:
47199
Reactions
L-rhamnose = L-rhamnulose.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + L-rhamnulose = ADP + L-rhamnulose 1- phosphate
Gene Name:
rhaB
Uniprot ID:
P32171
Molecular weight:
54069
Reactions
ATP + L-rhamnulose = ADP + L-rhamnulose 1-phosphate.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the phosphorylation of L-xylulose and 3-keto- L-gulonate. Is involved in L-lyxose utilization via xylulose, and may also be involved in the utilization of 2,3-diketo-L-gulonate
Gene Name:
lyx
Uniprot ID:
P37677
Molecular weight:
55155
Reactions
ATP + L-xylulose = ADP + L-xylulose 5-phosphate.
ATP + 3-dehydro-L-gulonate = ADP + 3-dehydro-L-gulonate 6-phosphate.

Transporters

General function:
Carbohydrate transport and metabolism
Specific function:
Part of the tripartite ATP-independent periplasmic (TRAP) transport system yiaMNO involved in the uptake of 2,3- diketo-L-gulonate
Gene Name:
yiaM
Uniprot ID:
P37674
Molecular weight:
17516
General function:
Carbohydrate transport and metabolism
Specific function:
Part of the tripartite ATP-independent periplasmic (TRAP) transport system yiaMNO involved in the uptake of 2,3- diketo-L-gulonate
Gene Name:
yiaN
Uniprot ID:
P37675
Molecular weight:
45368
General function:
Involved in transport
Specific function:
Part of the tripartite ATP-independent periplasmic (TRAP) transport system yiaMNO involved in the uptake of 2,3- diketo-L-gulonate. This protein specifically binds 2,3-diketo-L- gulonate. Is not able to bind either L-ascorbate or dehydroascorbate
Gene Name:
yiaO
Uniprot ID:
P37676
Molecular weight:
35970
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368