Xylulose 5-phosphate (ECMDB04178) (M2MDB000653)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:07:26 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:54:50 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Pentose phosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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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 D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate More...Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate D-Ribulose 5-phosphate <> Xylulose 5-phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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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