D-Erythrose 4-phosphate (ECMDB02649) (M2MDB000460)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:56:48 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:54:17 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | D-Erythrose 4-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C4H9O7P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 200.0838 Monoisotopic: 200.008589154 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | NGHMDNPXVRFFGS-IUYQGCFVSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 585-18-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 4-O-phosphono-D-erythrose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O[C@H](COP(O)(O)=O)[C@@H](O)C=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Monosaccharide 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: | D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate D-Erythrose 4-phosphate + Water + NAD <> 4-Phospho-D-erythronate +2 Hydrogen ion + NADH D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate Sedoheptulose 1,7-bisphosphate <> Dihydroxyacetone phosphate + D-Erythrose 4-phosphate Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate D-Erythrose 4-phosphate + NAD + Water <> 4-Phospho-D-erythronate + NADH + Hydrogen ion Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate D-Erythrose 4-phosphate + Water + NAD > 4-Phospho-D-erythronate + NADH + Hydrogen ion Dihydroxyacetone phosphate + D-Erythrose 4-phosphate < Sedoheptulose 1,7-bisphosphate Phosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphate D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Erythrose 4-phosphate + Fructose 6-phosphate D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> beta-D-Fructose 6-phosphate + D-Erythrose 4-phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphate Erythrose + Erythrose > D-Erythrose 4-phosphate + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/19:0cycv8c) + CL(17:0cycw7c/16:0/17:0cycw7c/16:1(9Z)) D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH +2 Hydrogen ion Sedoheptulose 1,7-bisphosphate > D-Erythrose 4-phosphate + Glycerone phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate D-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate More...Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate D-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
- Gene Name:
- aroH
- Uniprot ID:
- P00887
- Molecular weight:
- 38735
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
- Gene Name:
- aroF
- Uniprot ID:
- P00888
- Molecular weight:
- 38804
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
- Gene Name:
- talA
- Uniprot ID:
- P0A867
- Molecular weight:
- 35659
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
- Gene Name:
- talB
- Uniprot ID:
- P0A870
- Molecular weight:
- 35219
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
- Gene Name:
- fbaB
- Uniprot ID:
- P0A991
- Molecular weight:
- 38109
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
- Specific function:
- D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
- Gene Name:
- gapA
- Uniprot ID:
- P0A9B2
- Molecular weight:
- 35532
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH. |
- General function:
- Involved in erythrose-4-phosphate dehydrogenase activity
- Specific function:
- Catalyzes the NAD-dependent conversion of D-erythrose 4- phosphate to 4-phosphoerythronate
- Gene Name:
- epd
- Uniprot ID:
- P0A9B6
- Molecular weight:
- 37299
Reactions
D-erythrose 4-phosphate + NAD(+) + H(2)O = 4-phosphoerythronate + NADH. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
- Gene Name:
- fbaA
- Uniprot ID:
- P0AB71
- Molecular weight:
- 39147
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
- Gene Name:
- aroG
- Uniprot ID:
- P0AB91
- Molecular weight:
- 38009
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + 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 sugar:hydrogen symporter activity
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
- Gene Name:
- crr
- Uniprot ID:
- P69783
- Molecular weight:
- 18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine. |
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
- Gene Name:
- murP
- Uniprot ID:
- P77272
- Molecular weight:
- 49801
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
Transporters
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
- Gene Name:
- murP
- Uniprot ID:
- P77272
- Molecular weight:
- 49801
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |