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Showing metabocard for Fructose 6-phosphate (BMDB0000124)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2016-09-30 22:19:51 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2020-05-21 16:28:40 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BMDB ID | BMDB0000124 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Common Name | Fructose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Fructose 6-phosphate, also known as neuberg ester or D-fructose-6-p, 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. Fructose 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 6-phosphate exists in all living species, ranging from bacteria to humans. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms |
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Chemical Formula | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight | 260.1358 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight | 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS Registry Number | 643-13-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Identifier | 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key | GSXOAOHZAIYLCY-HSUXUTPPSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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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Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Status | Detected but not Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Origin |
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Biofunction | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Application | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular locations |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties |
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Predicted Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations |
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Biospecimen Locations |
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Pathways | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
HMDB ID | HMDB0000124 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
DrugBank ID | DB04493 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
FooDB ID | FDB021896 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KNApSAcK ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemspider ID | 62713 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Compound ID | C00085 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BioCyc ID | CPD-15709 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BiGG ID | 33795 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Wikipedia Link | Fructose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
METLIN ID | 5159 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PubChem Compound | 69507 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
ChEBI ID | 15946 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
General References |
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Enzymes
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
- Gene Name:
- TALDO1
- Uniprot ID:
- Q2TBL6
- Molecular weight:
- 37685.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
- Gene Name:
- TALDO1
- Uniprot ID:
- Q58DR3
- Molecular weight:
- 23712.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations and probably participates in glycogen synthesis from carbohydrate precursors, such as lactate.
- Gene Name:
- FBP2
- Uniprot ID:
- Q2KJJ9
- Molecular weight:
- 36767.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Synthesis and degradation of fructose 2,6-bisphosphate.
- Gene Name:
- PFKFB3
- Uniprot ID:
- Q28901
- Molecular weight:
- 53584.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Synthesis and degradation of fructose 2,6-bisphosphate.
- Gene Name:
- PFKFB2
- Uniprot ID:
- P26285
- Molecular weight:
- 60811.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations, acting as a rate-limiting enzyme in gluconeogenesis. Plays a role in regulating glucose sensing and insulin secretion of pancreatic beta-cells. Appears to modulate glycerol gluconeogenesis in liver. Important regulator of appetite and adiposity; increased expression of the protein in liver after nutrient excess increases circulating satiety hormones and reduces appetite-stimulating neuropeptides and thus seems to provide a feedback mechanism to limit weight gain.
- Gene Name:
- FBP1
- Uniprot ID:
- Q3SZB7
- Molecular weight:
- 36728.0
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphate | details |
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis (By similarity). Negatively regulates the phagocyte oxidative burst in response to bacterial infection by controlling cellular NADPH biosynthesis and NADPH oxidase-derived reactive oxygen species. Upon macrophage activation, drives the metabolic switch toward glycolysis, thus preventing glucose turnover that produces NADPH via pentose phosphate pathway (By similarity).
- Gene Name:
- PFKL
- Uniprot ID:
- A1A4J1
- Molecular weight:
- 85292.0
Reactions
Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADP | details |
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
- Gene Name:
- PFKM
- Uniprot ID:
- Q0IIG5
- Molecular weight:
- 85294.0
- General function:
- Energy production and conversion
- Specific function:
- Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
- Gene Name:
- TKT
- Uniprot ID:
- Q6B855
- Molecular weight:
- 67906.0
Reactions
D-Erythrose 4-phosphate + Xylulose 5-phosphate → Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate | details |
- General function:
- Cell wall/membrane/envelope biogenesis
- Specific function:
- Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins (By similarity).
- Gene Name:
- GFPT2
- Uniprot ID:
- Q08DQ2
- Molecular weight:
- 77081.0
Reactions
Fructose 6-phosphate + L-Glutamine → Glucosamine 6-phosphate + L-Glutamic acid | details |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
- Gene Name:
- HK1
- Uniprot ID:
- P27595
- Molecular weight:
- 103064.0
Reactions
D-Fructose + Adenosine triphosphate → Fructose 6-phosphate + ADP | details |
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions.
- Gene Name:
- MPI
- Uniprot ID:
- Q3SZI0
- Molecular weight:
- 46369.0
Reactions
Mannose 6-phosphate → Fructose 6-phosphate | details |
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- Fructose-bisphosphatase hydrolyzing fructose-2,6-bisphosphate as well as fructose-1,6-bisphosphate (By similarity). Acts as a negative regulator of glycolysis by lowering intracellular levels of fructose-2,6-bisphosphate in a p53/TP53-dependent manner, resulting in the pentose phosphate pathway (PPP) activation and NADPH production. Contributes to the generation of reduced glutathione to cause a decrease in intracellular reactive oxygen species (ROS) content, correlating with its ability to protect cells from oxidative or metabolic stress-induced cell death. Plays a role in promoting protection against cell death during hypoxia by decreasing mitochondria ROS levels in a HK2-dependent manner through a mechanism that is independent of its fructose-bisphosphatase activity. In response to cardiac damage stress, mediates p53-induced inhibition of myocyte mitophagy through ROS levels reduction and the subsequent inactivation of BNIP3. Reduced mitophagy results in an enhanced apoptotic myocyte cell death, and exacerbates cardiac damage. Plays a role in adult intestinal regeneration; contributes to the growth, proliferation and survival of intestinal crypts following tissue ablation. Plays a neuroprotective role against ischemic brain damage by enhancing PPP flux and preserving mitochondria functions. Protects glioma cells from hypoxia- and ROS-induced cell death by inhibiting glycolysis and activating mitochondrial energy metabolism and oxygen consumption in a TKTL1-dependent and p53/TP53-independent manner. Plays a role in cancer cell survival by promoting DNA repair through activating PPP flux in a CDK5-ATM-dependent signaling pathway during hypoxia and/or genome stress-induced DNA damage responses. Involved in intestinal tumor progression.
- Gene Name:
- TIGAR
- Uniprot ID:
- Q1JQA7
- Molecular weight:
- 29467.0
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- In the cytoplasm, catalyzes the conversion of glucose-6-phosphate to fructose-6-phosphate, the second step in glycolysis, and the reverse reaction during gluconeogenesis (By similarity). Besides it's role as a glycolytic enzyme, also acts as a secreted cytokine: acts as an angiogenic factor (AMF) that stimulates endothelial cell motility. Acts as a neurotrophic factor, neuroleukin, for spinal and sensory neurons. It is secreted by lectin-stimulated T-cells and induces immunoglobulin secretion (By similarity).
- Gene Name:
- GPI
- Uniprot ID:
- Q3ZBD7
- Molecular weight:
- 62855.0
Reactions
Fructose 6-phosphate → Glucose 6-phosphate | details |
Beta-D-Glucose 6-phosphate → Fructose 6-phosphate | details |
- General function:
- Not Available
- Specific function:
- Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
- Gene Name:
- GNPDA1
- Uniprot ID:
- A4FV08
- Molecular weight:
- 32580.0
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammonia | details |