D-Ribose-5-phosphate (ECMDB02033) (M2MDB000431)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:55:08 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-16 14:50:11 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | D-Ribose-5-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | D-ribose-5-phosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Ribose 5-phosphate is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose-5-phosphate. Ribulose-5-phosphate can reversibly isomerize to ribose-5-phosphate. Ribulose-5-phosphate can alternatively undergo a series of isomerizations as well as transaldolations and transketolations that result in the production of other pentoses phosphates as well as fructose 6-phosphate and glyceraldehyde-3-phosphate (both intermediates in glycolysis). The enzyme ribose-phosphate diphosphokinase converts ribose-5-phosphate into phosphoribosyl pyrophosphate. (WikiPedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H11O8P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 230.1098 Monoisotopic: 230.01915384 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | KTVPXOYAKDPRHY-SOOFDHNKSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5?/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 4151-19-3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | D-ribofuranose 5-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | D-Ribose-5-phosphate <> D-Ribulose 5-phosphate D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate Ribose-1-phosphate <> D-Ribose-5-phosphate Adenosine diphosphate ribose + Water <> Adenosine monophosphate +2 Hydrogen ion + D-Ribose-5-phosphate Water + D-Ribose-5-phosphate > Phosphate + Ribose Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Hydrogen ion + Phosphoribosyl pyrophosphate Adenosine monophosphate + Water <> Adenine + D-Ribose-5-phosphate Adenosine triphosphate + Ribose <> ADP + Hydrogen ion + D-Ribose-5-phosphate Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Phosphoribosyl pyrophosphate Adenosine triphosphate + Ribose <> ADP + D-Ribose-5-phosphate Adenosine diphosphate ribose + Water <> Adenosine monophosphate + D-Ribose-5-phosphate D-Ribose-5-phosphate <> D-Ribulose 5-phosphate alpha-D-Ribose 1-phosphate + Ribose-1-phosphate <> D-Ribose-5-phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate Aminofructose 6-phosphate + D-Ribose-5-phosphate <> Iminoerythrose 4-phosphate + Sedoheptulose 7-phosphate D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate Water + Adenosine monophosphate > D-Ribose-5-phosphate + Adenine Water + Nicotinamide ribotide <> Hydrogen ion + D-Ribose-5-phosphate + Niacinamide D-ribose + Adenosine triphosphate > Hydrogen ion + D-Ribose-5-phosphate + ADP Adenosine diphosphate ribose + Water > Hydrogen ion + Adenosine monophosphate + D-Ribose-5-phosphate D-Ribose-5-phosphate + Uracil <> Water + Pseudouridine 5'-phosphate Adenosine diphosphate ribose + Water > Adenosine monophosphate + D-Ribose-5-phosphate Ribose-1-phosphate > D-Ribose-5-phosphate Adenosine triphosphate + D-Ribose-5-phosphate > Adenosine monophosphate + Phosphoribosyl pyrophosphate Pseudouridine 5'-phosphate + Water > Uracil + D-Ribose-5-phosphate Adenosine triphosphate + Ribose > ADP + D-Ribose-5-phosphate More...D-Ribose-5-phosphate > D-Ribulose 5-phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Ribose-5-phosphate + Xylulose 5-phosphate D-Ribulose 5-phosphate <> D-Ribose-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 D-Ribose-5-phosphate + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Phosphoribosyl pyrophosphate D-Ribose-5-phosphate > Ribose-1-phosphate Ribose + Adenosine triphosphate > D-Ribose-5-phosphate + ADP + Hydrogen ion D-Ribose-5-phosphate <> D-Ribulose 5-phosphate Adenosine triphosphate + Ribose <> ADP + Hydrogen ion + D-Ribose-5-phosphate Adenosine monophosphate + Water <> Adenine + D-Ribose-5-phosphate Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Hydrogen ion + Phosphoribosyl pyrophosphate Adenosine diphosphate ribose + Water <> Adenosine monophosphate +2 Hydrogen ion + D-Ribose-5-phosphate D-Ribose-5-phosphate <> D-Ribulose 5-phosphate Adenosine triphosphate + Ribose <> ADP + Hydrogen ion + D-Ribose-5-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Phosphotransfer between the C1 and C5 carbon atoms of pentose
- Gene Name:
- deoB
- Uniprot ID:
- P0A6K6
- Molecular weight:
- 44370
Reactions
Alpha-D-ribose 1-phosphate = D-ribose 5-phosphate. |
2-deoxy-alpha-D-ribose 1-phosphate = 2-deoxy-alpha-D-ribose 5-phosphate. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- ATP + D-ribose 5-phosphate = AMP + 5-phospho- alpha-D-ribose 1-diphosphate
- Gene Name:
- prs
- Uniprot ID:
- P0A717
- Molecular weight:
- 34218
Reactions
ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in ribose-5-phosphate isomerase activity
- Specific function:
- D-ribose 5-phosphate = D-ribulose 5-phosphate
- Gene Name:
- rpiA
- Uniprot ID:
- P0A7Z0
- Molecular weight:
- 22860
Reactions
D-ribose 5-phosphate = D-ribulose 5-phosphate. |
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + D-ribose = ADP + D-ribose 5-phosphate
- Gene Name:
- rbsK
- Uniprot ID:
- P0A9J6
- Molecular weight:
- 32290
Reactions
ATP + D-ribose = ADP + D-ribose 5-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Involved in regulation of AMP concentrations
- Gene Name:
- amn
- Uniprot ID:
- P0AE12
- Molecular weight:
- 53994
Reactions
AMP + H(2)O = D-ribose 5-phosphate + adenine. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Uniprot ID:
- P0AE22
- Molecular weight:
- 26103
Reactions
A phosphate monoester + H(2)O = an alcohol + 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 intramolecular transferase activity, phosphotransferases
- Specific function:
- This enzyme participates in both the breakdown and synthesis of glucose
- Gene Name:
- pgm
- Uniprot ID:
- P36938
- Molecular weight:
- 58361
Reactions
Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate. |
- General function:
- Involved in carbohydrate metabolic process
- Specific function:
- In addition to its activity on D-ribose 5-phosphate it probably also has activity on D-allose 6-phosphate
- Gene Name:
- rpiB
- Uniprot ID:
- P37351
- Molecular weight:
- 16073
Reactions
D-ribose 5-phosphate = D-ribulose 5-phosphate. |
D-allose 6-phosphate = D-allulose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the hydrolysis of sugar phosphate to sugar and inorganic phosphate. Has a wide substrate specificity catalyzing the hydrolysis of fructose-1-P most efficiently, but it remains uncertain if this is the real substrate in vivo
- Gene Name:
- supH
- Uniprot ID:
- P75792
- Molecular weight:
- 30413
Reactions
Sugar phosphate + H(2)O = sugar + phosphate. |
- General function:
- Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
- Specific function:
- Acts on ADP-mannose and ADP-glucose as well as ADP- ribose. Prevents glycogen biosynthesis. The reaction catalyzed by this enzyme is a limiting step of the gluconeogenic process
- Gene Name:
- nudF
- Uniprot ID:
- Q93K97
- Molecular weight:
- 23667
Reactions
ADP-ribose + H(2)O = AMP + D-ribose 5-phosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Active on adenosine(5')triphospho(5')adenosine (Ap3A), ADP-ribose, NADH, adenosine(5')diphospho(5')adenosine (Ap2A)
- Gene Name:
- nudE
- Uniprot ID:
- P45799
- Molecular weight:
- 21153
Reactions
ADP-ribose + H(2)O = AMP + D-ribose 5-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Specific function unknown
- Gene Name:
- yhfW
- Uniprot ID:
- P45549
- Molecular weight:
- 44559
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368