Record Information
Version2.0
Creation Date2012-05-31 14:07:26 -0600
Update Date2015-06-03 15:54:50 -0600
Secondary Accession Numbers
  • ECMDB04178
Identification
Name:Xylulose 5-phosphate
DescriptionXylulose 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 carbohydrates to cells 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; EC 2.7.1.11] in glycolysis and will increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358)
Structure
Thumb
Synonyms:
  • 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
  • X5P
  • Xu-5-P
  • Xylulose 5-phosphate
  • Xylulose 5-phosphoric acid
  • Xylulose-P
  • Xylulose-phosphate
  • Xylulose-phosphoric acid
Chemical Formula:C5H11O8P
Weight:Average: 230.1098
Monoisotopic: 230.01915384
InChI Key:FNZLKVNUWIIPSJ-RFZPGFLSSA-N
InChI:InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1
CAS number:4212-65-1
IUPAC Name:{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Name:ribulose-5-phosphate
SMILES:OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-3.209PhysProp
Predicted Properties
PropertyValueSource
Water Solubility26.1 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.47 m³·mol⁻¹ChemAxon
Polarizability18.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + D-Xylulose <> ADP + Hydrogen ion + Xylulose 5-phosphate
D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate
L-Ribulose 5-phosphate <> Xylulose 5-phosphate
D-Ribulose 5-phosphate <> Xylulose 5-phosphate
Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate
D-Ribulose 5-phosphate <> Xylulose 5-phosphate
Adenosine triphosphate + D-Xylulose <> ADP + Xylulose 5-phosphate
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate
beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate
D-Xylulose + Adenosine triphosphate > Hydrogen ion + Xylulose 5-phosphate + ADP
L-Ribulose 5-phosphate > Xylulose 5-phosphate
D-Ribulose 5-phosphate > Xylulose 5-phosphate
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Ribose-5-phosphate + Xylulose 5-phosphate
Adenosine triphosphate + D-Xylulose > ADP + Xylulose 5-phosphate
D-Ribulose 5-phosphate <> Xylulose 5-phosphate + Xylulose 5-phosphate
Xylulose 5-phosphate + D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate
L-Threo-2-pentulose + Adenosine triphosphate + L-Threo-2-pentulose > Xylulose 5-phosphate + Adenosine diphosphate + Xylulose 5-phosphate + ADP
3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > Xylulose 5-phosphate + Carbon dioxide + Xylulose 5-phosphate
2,3-Diketo-L-gulonate + Hydrogen ion + 2,3-Diketo-L-gulonate > Carbon dioxide + Xylulose 5-phosphate + Xylulose 5-phosphate
Xylulose 5-phosphate + Xylulose 5-phosphate > L-ribulose 5-phosphate + L-ribulose 5-phosphate
L-ribulose 5-phosphate + L-ribulose 5-phosphate > Xylulose 5-phosphate + Xylulose 5-phosphate
L-Threo-2-pentulose + Adenosine triphosphate > Xylulose 5-phosphate + ADP + Hydrogen ion
L-ribulose 5-phosphate <> Xylulose 5-phosphate

SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
L-arabinose Degradation IPW002103 ThumbThumb?image type=greyscaleThumb?image type=simple
L-lyxose DegradationPW002100 ThumbThumb?image type=greyscaleThumb?image type=simple
Pentose PhosphatePW000893 ThumbThumb?image type=greyscaleThumb?image type=simple
Xylose Degradation IPW002105 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0592-9800000000-d336b0e2eff1402939d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-9023200000-1dd7d8e1f64921beb234View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3790000000-6f5913e9948fa7667e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-9710000000-3724bb9f611bbdc1fe11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-8bc9cecb2dddad8ca5e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9520000000-c36fdbcc1d3b19b2fafdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b67b8ea484aa4ddb40e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b17cf4f5a8c927fe64View in MoNA
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
  • Himmo SD, Thomson M, Gubler CJ: Isolation of transketolase from human erythrocytes. Prep Biochem. 1988;18(3):261-76. Pubmed: 3237644
  • 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
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. Pubmed: 16077128
  • 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
  • Veech, R. L. (2003). "A humble hexose monophosphate pathway metabolite regulates short- and long-term control of lipogenesis." Proc Natl Acad Sci U S A 100:5578-5580. Pubmed: 12721358
  • Williams DG: Effect of added xylulose-5-phosphate on the assay of erythrocyte transketolase. Clin Chem. 1977 Jul;23(7):1368. Pubmed: 872397
  • 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:Shaeri, Jobin; Wohlgemuth, Roland; Woodley, John M. Semiquantitative Process Screening for the Biocatalytic Synthesis of D-Xylulose-5-phosphate. Organic Process Research & Development (2006), 10(3), 605-610.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16332
HMDB IDHMDB00868
Pubchem Compound ID850
Kegg IDC00231
ChemSpider ID388330
WikipediaXylulose 5-phosphate
BioCyc IDXYLULOSE-5-PHOSPHATE
EcoCyc IDXYLULOSE-5-PHOSPHATE
Ligand Expo5SP

Enzymes

General function:
Involved in metal ion binding
Specific function:
L-ribulose 5-phosphate = D-xylulose 5- phosphate
Gene Name:
araD
Uniprot ID:
P08203
Molecular weight:
25519
Reactions
L-ribulose 5-phosphate = D-xylulose 5-phosphate.
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 catalytic activity
Specific function:
D-ribulose 5-phosphate = D-xylulose 5- phosphate
Gene Name:
rpe
Uniprot ID:
P0AG07
Molecular weight:
24554
Reactions
D-ribulose 5-phosphate = D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
tktA
Uniprot ID:
P27302
Molecular weight:
72211
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
tktB
Uniprot ID:
P33570
Molecular weight:
73042
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-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.
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).
General function:
Involved in metal ion binding
Specific function:
Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. May be involved in the utilization of 2,3- diketo-L-gulonate
Gene Name:
sgbE
Uniprot ID:
P37680
Molecular weight:
25561
Reactions
L-ribulose 5-phosphate = D-xylulose 5-phosphate.
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).
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.
General function:
Involved in metal ion binding
Specific function:
Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. Is involved in the anaerobic L-ascorbate utilization
Gene Name:
ulaF
Uniprot ID:
P39306
Molecular weight:
25278
Reactions
L-ribulose 5-phosphate = D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Probable pentose-5-phosphate 3-epimerase
Gene Name:
sgcE
Uniprot ID:
P39362
Molecular weight:
23214