| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:28 -0700 |
| HMDB ID |
HMDB00868 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
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 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- D-Xylulose 5-phosphate
- D-Xylulose 5-PO4
- D-Xylulose-5-P
- D-Xylulose-5-phosphate
- Xu-5-P
- Xylulose 5-phosphate
- Xylulose-P
- Xylulose-phosphate
|
| Chemical Formula |
C5H11O8P |
| Average Molecular Weight |
230.1098 |
| Monoisotopic Molecular Weight |
230.01915384 |
| 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 Number |
4212-65-1 |
| 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 Key |
FNZLKVNUWIIPSJ-RFZPGFLSSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Monosaccharides |
| Sub Class |
Pentoses |
| 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
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| Direct Parent |
Pentoses |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
|---|
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
Not Available
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| Pathways |
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| Normal Concentrations |
|---|
|
| Cellular Cytoplasm |
Detected and Quantified |
|
0.43 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022290 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
388330 |
| KEGG Compound ID |
C00231 |
| BioCyc ID |
XYLULOSE-5-PHOSPHATE |
| BiGG ID |
34329 |
| Wikipedia Link |
Xylulose 5-phosphate |
| NuGOwiki Link |
HMDB00868 |
| Metagene Link |
HMDB00868 |
| METLIN ID |
5829 |
| PubChem Compound |
439190 |
| PDB ID |
5SP |
| ChEBI ID |
16332 |
| References |
|---|
| 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
|
| General References |
- 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
- Williams DG: Effect of added xylulose-5-phosphate on the assay of erythrocyte transketolase. Clin Chem. 1977 Jul;23(7):1368.
Pubmed: 872397
- 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
- Himmo SD, Thomson M, Gubler CJ: Isolation of transketolase from human erythrocytes. Prep Biochem. 1988;18(3):261-76.
Pubmed: 3237644
|
