Fructose 6-phosphate (ECMDB00124) (M2MDB000047)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:21:23 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Fructose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Fructose-6-phosphate is an important intermediate in glycolysis and gluconeogenesis. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 260.1358 Monoisotopic: 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | GSXOAOHZAIYLCY-HSUXUTPPSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 643-13-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | D-fructose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose 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 | Hexose 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: | Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate Phosphoenolpyruvic acid + D-Fructose > Fructose 6-phosphate + Pyruvic acid D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate + Hydrogen ion Glucosamine 6-phosphate + Water > Fructose 6-phosphate + Ammonium Fructose 6-phosphate + Water > D-Fructose + Phosphate Mannose 6-phosphate <> Fructose 6-phosphate NAD + Sorbitol-6-phosphate <> Fructose 6-phosphate + Hydrogen ion + NADH Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamate Glucose 6-phosphate <> Fructose 6-phosphate D-Allulose-6-phosphate <> Fructose 6-phosphate Glucosamine 6-phosphate + Water <> Fructose 6-phosphate + Ammonia Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Phosphate Glucosamine 6-phosphate + Water <> Hydrogen ion + Fructose 6-phosphate + Ammonia Fructose 6-phosphate + L-Glutamine > Glucosamine 6-phosphate + L-Glutamate D-Allulose-6-phosphate > Fructose 6-phosphate D-fructose + Phosphoenolpyruvic acid > Fructose 6-phosphate + Pyruvic acid Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Inorganic phosphate Fructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphate Glucose 6-phosphate > Fructose 6-phosphate L-Glutamine + Fructose 6-phosphate > L-Glutamate + D-glucosamine 6-phosphate Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate More...Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate Mannose 6-phosphate > Fructose 6-phosphate Mannitol 1-phosphate + NAD > Fructose 6-phosphate + NADH D-glucosamine 6-phosphate + Water > Fructose 6-phosphate + Ammonia Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADH Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Erythrose 4-phosphate + Fructose 6-phosphate Adenosine triphosphate + D-Fructose <> ADP + Fructose 6-phosphate Adenosine triphosphate + Fructose 6-phosphate <> ADP + Fructose 1,6-bisphosphate Sorbitol 6-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion Mannitol 1-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion beta-D-Glucose 6-phosphate > Fructose 6-phosphate + Fructose 6-phosphate Fructose 6-phosphate + Phosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Water + Fructose 1,6-bisphosphate Fructose 6-phosphate + Adenosine triphosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP Fructose 6-phosphate + L-Glutamine + Fructose 6-phosphate > L-Glutamic acid + Glucosamine 6-phosphate + L-Glutamate Fructose 6-phosphate + NADH + Hydrogen ion + Fructose 6-phosphate <> NAD + Mannitol 1-phosphate D-Fructose + HPr - phosphorylated + D-Fructose > HPr + Fructose 6-phosphate + Fructose 6-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 Glucosamine 6-phosphate + Water <> Fructose 6-phosphate + Ammonia Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate Glucosamine 6-phosphate + Water <> Fructose 6-phosphate + Ammonia Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in mannose-6-phosphate isomerase activity
- Specific function:
- Involved in the conversion of glucose to GDP-L-fucose, which can be converted to L-fucose, a capsular polysaccharide
- Gene Name:
- manA
- Uniprot ID:
- P00946
- Molecular weight:
- 42850
Reactions
D-mannose 6-phosphate = D-fructose 6-phosphate. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
- Gene Name:
- srlD
- Uniprot ID:
- P05707
- Molecular weight:
- 27858
Reactions
D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH. |
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
- Gene Name:
- pfkB
- Uniprot ID:
- P06999
- Molecular weight:
- 32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate. |
- General function:
- Involved in transferase activity, transferring phosphorus-containing groups
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
- Gene Name:
- ptsI
- Uniprot ID:
- P08839
- Molecular weight:
- 63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine. |
- General function:
- Involved in oxidation-reduction process
- Specific function:
- D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
- Gene Name:
- mtlD
- Uniprot ID:
- P09424
- Molecular weight:
- 41139
Reactions
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH. |
- General function:
- Involved in glucose-6-phosphate isomerase activity
- Specific function:
- D-glucose 6-phosphate = D-fructose 6- phosphate
- Gene Name:
- pgi
- Uniprot ID:
- P0A6T1
- Molecular weight:
- 61529
Reactions
D-glucose 6-phosphate = D-fructose 6-phosphate. |
- General function:
- Involved in carbohydrate metabolic process
- Specific function:
- Catalyzes the reversible isomerization-deamination of glucosamine 6-phosphate (GlcN6P) to form fructose 6-phosphate (Fru6P) and ammonium ion
- Gene Name:
- nagB
- Uniprot ID:
- P0A759
- Molecular weight:
- 29774
Reactions
D-glucosamine 6-phosphate + H(2)O = D-fructose 6-phosphate + NH(3). |
- General function:
- Involved in ATP binding
- Specific function:
- ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
- Gene Name:
- pfkA
- Uniprot ID:
- P0A796
- Molecular weight:
- 34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate. |
- 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 phosphoric ester hydrolase activity
- Specific function:
- D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
- Gene Name:
- fbp
- Uniprot ID:
- P0A993
- Molecular weight:
- 36834
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate. |
- General function:
- Involved in glycerol metabolic process
- Specific function:
- D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
- Gene Name:
- glpX
- Uniprot ID:
- P0A9C9
- Molecular weight:
- 35852
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate. |
- General function:
- Involved in metabolic process
- Specific function:
- Catalyzes the first step in hexosamine metabolism, converting fructose-6P into glucosamine-6P using glutamine as a nitrogen source
- Gene Name:
- glmS
- Uniprot ID:
- P17169
- Molecular weight:
- 66894
Reactions
L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates pyridoxalphosphate and erythrose 4-phosphate
- Gene Name:
- ybhA
- Uniprot ID:
- P21829
- Molecular weight:
- 30201
- General function:
- Transcription
- Specific function:
- Catalyzes the phosphorylation of fructose to fructose-6- P. Has also low level glucokinase activity in vitro. Is not able to phosphorylate D-ribose, D-mannitol, D-sorbitol, inositol, and L-threonine
- Gene Name:
- mak
- Uniprot ID:
- P23917
- Molecular weight:
- 32500
Reactions
ATP + D-fructose = ADP + D-fructose 6-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:
- Specific function unknown
- Gene Name:
- alsE
- Uniprot ID:
- P32719
- Molecular weight:
- 26109
- 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 phosphoenolpyruvate-dependent sugar phosphotransferase system
- 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 mannose transport
- Gene Name:
- manX
- Uniprot ID:
- P69797
- Molecular weight:
- 35047
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine. |
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar 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 phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
- Gene Name:
- manY
- Uniprot ID:
- P69801
- Molecular weight:
- 27636
- General function:
- Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
- Gene Name:
- manZ
- Uniprot ID:
- P69805
- Molecular weight:
- 31303
- General function:
- Involved in glycerol metabolic process
- Specific function:
- Specific function unknown
- Gene Name:
- yggF
- Uniprot ID:
- P21437
- Molecular weight:
- 34323
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
- Gene Name:
- fsaB
- Uniprot ID:
- P32669
- Molecular weight:
- 23555
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
- Gene Name:
- fsaA
- Uniprot ID:
- P78055
- Molecular weight:
- 22997
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in sugar:hydrogen symporter activity
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
- Gene Name:
- ptsH
- Uniprot ID:
- P0AA04
- Molecular weight:
- 9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine. |
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- cobB
- Uniprot ID:
- P75960
- Molecular weight:
- Not Available
Transporters
- General function:
- Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
- Gene Name:
- manY
- Uniprot ID:
- P69801
- Molecular weight:
- 27636
- General function:
- Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
- Gene Name:
- manZ
- Uniprot ID:
- P69805
- Molecular weight:
- 31303
- 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 transmembrane transport
- Specific function:
- Transport protein for sugar phosphate uptake
- Gene Name:
- uhpT
- Uniprot ID:
- P0AGC0
- Molecular weight:
- 50606
- 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