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L-Xylulose 5-phosphate (M2MDB001016)

Record Information
Version2.0
Creation Date2012-05-31 14:31:10 -0600
Update Date2015-09-18 15:17:18 -0600
Secondary Accession Numbers
  • ECMDB20169
Identification
Name:L-Xylulose 5-phosphate
Description)Xylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Pentulose, 5-(dihydrogen phosphate)
  • 2-Pentulose, 5-(dihydrogen phosphoric acid)
  • D-Ribulose-5-P
  • D-Ribulose-5-phosphate
  • D-Ribulose-5-phosphoric acid
  • D-Xylulose 5-phosphate
  • D-Xylulose 5-phosphoric acid
  • D-Xylulose 5-PO4
  • D-Xylulose-5-P
  • D-Xylulose-5-phosphate
  • D-Xylulose-5-phosphoric acid
  • L-RIBULOSE-5-P
  • L-Ribulose-5-phosphate
  • L-Ribulose-5-phosphoric acid
  • L-X5P
  • L-Xylulose 5-phosphoric acid
  • L-XYLULOSE-5-P
  • L-Xylulose-5-phosphate
  • L-Xylulose-5-phosphoric acid
  • Ribulose-5-P
  • Ribulose-5-Phosphate
  • Ribulose-5-phosphoric acid
  • RIBULOSE-5P
  • Xu-5-P
  • Xylulose 5-phosphate
  • Xylulose 5-phosphoric acid
  • Xylulose-5-P
  • Xylulose-5-phosphate
  • Xylulose-5-phosphoric acid
  • Xylulose-p
  • Xylulose-phosphate
  • Xylulose-phosphoric acid
  • [(2R,3R)-2,3,5-trihydroxy-4-oxopentyl] dihydrogen phosphate
  • [(2R,3R)-2,3,5-Trihydroxy-4-oxopentyl] dihydrogen phosphoric acid
Chemical Formula:C7H13O6P
Weight:Average: 224.15
Monoisotopic: 224.046072296
InChI Key:GOBYCGYLQSIFMQ-UHFFFAOYSA-L
InChI:InChI=1S/C7H15O6P/c1-5(4-13-14(10,11)12)6(2)7(9)3-8/h5-6,8H,3-4H2,1-2H3,(H2,10,11,12)/p-2
CAS number:60802-29-1
IUPAC Name:1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
Traditional IUPAC Name:1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
SMILES:CC(COP([O-])([O-])=O)C(C)C(=O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl phosphates. These are organic compounds containing a phosphate group that is linked to one or more alkyl chains.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAlkyl phosphates
Alternative Parents
Substituents
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility38.5 g/LALOGPS
logP-0.42ALOGPS
logP-0.22ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.73 m³·mol⁻¹ChemAxon
Polarizability19.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + L-Threo-2-pentulose <> ADP + Hydrogen ion + L-Xylulose 5-phosphate
3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion <> Carbon dioxide + L-Xylulose 5-phosphate
L-Xylulose 5-phosphate <> L-Ribulose 5-phosphate
Adenosine triphosphate + L-Threo-2-pentulose <> ADP + L-Xylulose 5-phosphate
L-Ribulose 5-phosphate <> L-Xylulose 5-phosphate
L-Ribulose 5-phosphate < L-Xylulose 5-phosphate
L-xylulose + Adenosine triphosphate > Hydrogen ion + L-Xylulose 5-phosphate + ADP
Hydrogen ion + 3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide
Adenosine triphosphate + L-Threo-2-pentulose > ADP + L-Xylulose 5-phosphate
3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide
L-Ribulose 5-phosphate > L-Xylulose 5-phosphate
3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + Carbon dioxide + L-Xylulose 5-phosphate
3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + L-Xylulose 5-phosphate
L-xylulose -5-phosphate + L-Xylulose 5-phosphate > L-ribulose 5-phosphate + L-ribulose 5-phosphate
L-Threo-2-pentulose + Adenosine triphosphate > L-Xylulose 5-phosphate + ADP + Hydrogen ion
L-Xylulose 5-phosphate > L-ribulose 5-phosphate
SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
L-lyxose DegradationPW002100 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Ascorbate and aldarate metabolism ec00053
  • Metabolic pathways eco01100
  • Microbial metabolism in diverse environments ec01120
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:
  • L-ascorbate degradation I (bacterial, anaerobic) PWY0-301
  • L-ascorbate degradation II (bacterial, aerobic) PWY-6961
  • L-lyxose degradation LYXMET-PWY
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1020± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
686± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1320± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16593
HMDB IDNot Available
Pubchem Compound ID850
Kegg IDC03291
ChemSpider ID827
Wikipedia IDNot Available
BioCyc IDL-XYLULOSE-5-P
EcoCyc IDL-XYLULOSE-5-P

Enzymes

Protein Details
1. Ribulokinase
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.
Protein Details
2. L-xylulose/3-keto-L-gulonate kinase
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.
Protein Details
3. 3-keto-L-gulonate-6-phosphate decarboxylase sgbH
General function:
Involved in catalytic activity
Specific function:
Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. May be involved in the utilization of 2,3- diketo-L-gulonate
Gene Name:
sgbH
Uniprot ID:
P37678
Molecular weight:
23445
Reactions
3-dehydro-L-gulonate 6-phosphate = L-xylulose 5-phosphate + CO(2).
Protein Details
4. 3-keto-L-gulonate-6-phosphate decarboxylase ulaD
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. Is involved in the anaerobic L-ascorbate utilization
Gene Name:
ulaD
Uniprot ID:
P39304
Molecular weight:
23578
Reactions
3-dehydro-L-gulonate 6-phosphate = L-xylulose 5-phosphate + CO(2).
Protein Details
5. L-ribulose-5-phosphate 3-epimerase ulaE
General function:
Involved in intramolecular oxidoreductase activity, interconverting aldoses and ketoses
Specific function:
Catalyzes the isomerization of L-xylulose-5-phosphate to L-ribulose-5-phosphate. Is involved in the anaerobic L-ascorbate utilization
Gene Name:
ulaE
Uniprot ID:
P39305
Molecular weight:
32006
Reactions
L-ribulose 5-phosphate = L-xylulose 5-phosphate.
Protein Details
6. predicted L-xylulose 5-phosphate 3-epimerase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yiaR
Uniprot ID:
P37679
Molecular weight:
Not Available