Glucose 6-phosphate (ECMDB01401) (M2MDB000372)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:51:48 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:54:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 260.1358 Monoisotopic: 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | NBSCHQHZLSJFNQ-GASJEMHNSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 56-73-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Liquid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acid Glucose 1-phosphate <> Glucose 6-phosphate Glucose 6-phosphate + Water > D-Glucose + Phosphate Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + Hydrogen ion + NADPH Glucose 6-phosphate + UDP-Glucose > Hydrogen ion + Trehalose 6-phosphate + Uridine 5'-diphosphate Adenosine triphosphate + D-Glucose > ADP + Glucose 6-phosphate + Hydrogen ion Arbutin 6-phosphate + Water > Glucose 6-phosphate + Hydroquinone Fructoselysine-6-phosphate + Water <> Glucose 6-phosphate + L-Lysine Glucose 6-phosphate <> Fructose 6-phosphate Water + Trehalose 6-phosphate > Glucose 6-phosphate + D-Glucose Adenosine triphosphate + D-Glucose <> ADP + D-Hexose 6-phosphate + Glucose 6-phosphate Adenosine triphosphate + alpha-D-Glucose <> ADP + Glucose 6-phosphate UDP-Glucose + Glucose 6-phosphate <> Uridine 5'-diphosphate + Trehalose 6-phosphate Protein N(pi)-phospho-L-histidine + D-Glucose <> Protein histidine + Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate Glucose 6-phosphate <> beta-D-Fructose 6-phosphate Glucose 1-phosphate <> D-Hexose 6-phosphate + Glucose 6-phosphate Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acid Cellobiose-6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose beta-D-Glucose 1-phosphate Glucose 6-phosphate b-D-Glucose + Adenosine triphosphate > Hydrogen ion + Glucose 6-phosphate + ADP α-D-glucose 6-phosphate <> Glucose 6-phosphate Salicin 6-phosphate + Water > Glucose 6-phosphate + salicyl alcohol Trehalose 6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose 6-Phospho-beta-D-glucosyl-(1,4)-D-glucose + Water > D-Glucose + Glucose 6-phosphate Fructoselysine-6-phosphate + Water > Glucose 6-phosphate + L-Lysine More...Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH Glucose 6-phosphate > Fructose 6-phosphate Adenosine triphosphate + D-Glucose > ADP + Glucose 6-phosphate UDP-Glucose + Glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate Cellobiose-6-phosphate + Water <> D-Glucose + Glucose 6-phosphate Trehalose 6-phosphate + Water <> D-Glucose + Glucose 6-phosphate Beta-D-Glucopyranuronic acid + Adenosine triphosphate > Glucose 6-phosphate + ADP + Hydrogen ion Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate Glucose 6-phosphate <> beta-D-Fructose 6-phosphate Glucose 1-phosphate <> Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate Glucose 1-phosphate <> Glucose 6-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: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- 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 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 glucokinase activity
- Specific function:
- Not highly important in E.coli as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
- Gene Name:
- glk
- Uniprot ID:
- P0A6V8
- Molecular weight:
- 34723
Reactions
ATP + D-glucose = ADP + D-glucose 6-phosphate. |
- General function:
- Involved in carbohydrate binding
- Specific function:
- Catalyzes the conversion of fructoselysine 6-phosphate to glucose 6-phosphate and lysine
- Gene Name:
- frlB
- Uniprot ID:
- P0AC00
- Molecular weight:
- 38569
Reactions
Fructoselysine 6-phosphate + H(2)O = glucose 6-phosphate + L-lysine. |
- General function:
- Involved in glucose-6-phosphate dehydrogenase activity
- Specific function:
- D-glucose 6-phosphate + NADP(+) = D-glucono- 1,5-lactone 6-phosphate + NADPH
- Gene Name:
- zwf
- Uniprot ID:
- P0AC53
- Molecular weight:
- 55704
Reactions
D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Can hydrolyze salicin and arbutin
- Gene Name:
- bglB
- Uniprot ID:
- P11988
- Molecular weight:
- 53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
- Gene Name:
- chbF
- Uniprot ID:
- P17411
- Molecular weight:
- 50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
- Gene Name:
- malX
- Uniprot ID:
- P19642
- Molecular weight:
- 56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Can hydrolyze salicin, cellobiose, and probably arbutin
- Gene Name:
- ascB
- Uniprot ID:
- P24240
- Molecular weight:
- 53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Alpha,alpha-trehalose 6-phosphate + H(2)O = D- glucose + D-glucose 6-phosphate
- Gene Name:
- treC
- Uniprot ID:
- P28904
- Molecular weight:
- 63837
Reactions
Alpha,alpha-trehalose 6-phosphate + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength
- Gene Name:
- otsA
- Uniprot ID:
- P31677
- Molecular weight:
- 53611
Reactions
UDP-glucose + D-glucose 6-phosphate = UDP + alpha,alpha-trehalose 6-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 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 glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
- Gene Name:
- ptsG
- Uniprot ID:
- P69786
- Molecular weight:
- 50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar 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 beta-phosphoglucomutase activity
- Specific function:
- Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
- Gene Name:
- ycjU
- Uniprot ID:
- P77366
- Molecular weight:
- 23565
Reactions
Beta-D-glucose 1-phosphate = beta-D-glucose 6-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- 6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
- Gene Name:
- bglA
- Uniprot ID:
- Q46829
- Molecular weight:
- 55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-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 catalytic activity
- Specific function:
- Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates fructose 1-phosphate and 6-phosphogluconate
- Gene Name:
- yqaB
- Uniprot ID:
- P77475
- Molecular weight:
- 20780
- 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:
- yeaD
- Uniprot ID:
- P39173
- Molecular weight:
- Not Available
Transporters
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
- Gene Name:
- malX
- Uniprot ID:
- P19642
- Molecular weight:
- 56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- 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 glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
- Gene Name:
- ptsG
- Uniprot ID:
- P69786
- Molecular weight:
- 50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + 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 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