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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:29:26 UTC
HMDB IDHMDB00868
Secondary Accession Numbers
  • HMDB06212
Metabolite Identification
Common NameXylulose 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 carbohydrate causes levels of liver 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 promotes the action of the transcription factor carbohydrate responsive element binding protein (ChREBP) to 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
  1. D-Xylulose 5-phosphate
  2. D-Xylulose 5-PO4
  3. D-Xylulose-5-P
  4. D-Xylulose-5-phosphate
  5. Xu-5-P
  6. Xylulose 5-phosphate
  7. Xylulose-P
  8. Xylulose-phosphate
Chemical FormulaC5H11O8P
Average Molecular Weight230.1098
Monoisotopic Molecular Weight230.01915384
IUPAC Name{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxyphosphonic acid
CAS Registry Number4212-65-1
SMILES
OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
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
InChI KeyFNZLKVNUWIIPSJ-RFZPGFLSSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monosaccharide Phosphates
  • ribulose 5-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Acyloin
  • Alpha Ketoaldehyde
  • Beta Ketoaldehyde
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area144.52ChemAxon
rotatable bond count6ChemAxon
refractivity42.47ChemAxon
polarizability18.08ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified0.43 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022290
KNApSAcK IDNot Available
Chemspider ID388330
KEGG Compound IDC00231
BioCyc IDXYLULOSE-5-PHOSPHATE
BiGG ID34329
Wikipedia LinkXylulose 5-phosphate
NuGOwiki LinkHMDB00868
Metagene LinkHMDB00868
METLIN ID5829
PubChem Compound439190
PDB ID5SP
ChEBI ID16332
References
Synthesis ReferenceShaeri, 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
General References
  1. 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
  2. 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
  3. Williams DG: Effect of added xylulose-5-phosphate on the assay of erythrocyte transketolase. Clin Chem. 1977 Jul;23(7):1368. Pubmed: 872397
  4. Himmo SD, Thomson M, Gubler CJ: Isolation of transketolase from human erythrocytes. Prep Biochem. 1988;18(3):261-76. Pubmed: 3237644
  5. Veech RL: A humble hexose monophosphate pathway metabolite regulates short- and long-term control of lipogenesis. Proc Natl Acad Sci U S A. 2003 May 13;100(10):5578-80. Epub 2003 Apr 29. Pubmed: 12721358

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:
TKTL1
Uniprot ID:
P51854
Molecular weight:
59302.195
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Not Available
Gene Name:
XYLB
Uniprot ID:
O75191
Molecular weight:
58381.695
Reactions
Adenosine triphosphate + D-Xylulose → ADP + Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
RPE
Uniprot ID:
Q53TV9
Molecular weight:
19537.4
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible epimerization of D-ribulose 5-phosphate to D-xylulose 5-phosphate.
Gene Name:
RPE
Uniprot ID:
Q96AT9
Molecular weight:
19537.385
Reactions
D-Ribulose 5-phosphate → Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis.
Gene Name:
TKTL2
Uniprot ID:
Q9H0I9
Molecular weight:
67876.625
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails