P. aeruginosa Metabolome Database: Glucose 6-phosphate (PAMDB000372)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000372

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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

β-D-glucose-6-P
A-D-glucose 6- phosphate
a-D-Glucose 6- phosphoric acid
A-D-Glucose 6-phosphate
a-D-Glucose 6-phosphoric acid
A-D-Glucose-6-phosphate
a-D-Glucose-6-phosphoric acid
a-D-Hexose 6-phosphate
a-D-Hexose 6-phosphoric acid
Alpha-D-Glucose 6-phosphate
alpha-D-Glucose 6-phosphoric acid
Alpha-D-Hexose 6-phosphate
alpha-D-Hexose 6-phosphoric acid
b-D-Glucose-6-P
Beta-D-Glucose-6-P
D(+)-Glucopyranose 6-phosphate
D(+)-Glucopyranose 6-phosphoric acid
D-Glucose 6-phosphate
D-Glucose 6-phosphoric acid
D-Glucose-6-dihydrogen phosphate
D-Glucose-6-dihydrogen phosphoric acid
D-Glucose-6-P
D-Glucose-6-phosphate
D-Glucose-6-phosphoric acid
D-Hexose 6-phosphate
D-Hexose 6-phosphoric acid
Glucose 6-phosphate
Glucose 6-phosphoric acid
Glucose-6-P
Glucose-6-phosphate
Glucose-6-phosphoric acid
Robison ester
α-D-Glucose 6-phosphate
α-D-Glucose 6-phosphoric acid
α-D-Hexose 6-phosphate
α-D-Hexose 6-phosphoric acid
β-D-Glucose-6-P

Chemical Formula:

C₆H₁₃O₉P

Average Molecular Weight:

260.1358

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Secondary alcohol
Polyol
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-hexopyranose 6-phosphate (CHEBI:4170 )
D-glucose 6-phosphate (CHEBI:4170 )

Physical Properties

State:

Liquid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	31.4 mg/mL	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol^-1	ChemAxon
Polarizability	20.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

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
Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH
Adenosine triphosphate + D-Glucose > ADP + Glucose 6-phosphate
Cellobiose-6-phosphate + Water <> D-Glucose + Glucose 6-phosphate

More...

Pathways:

Amino sugar and nucleotide sugar metabolism pae00520
Butirosin and neomycin biosynthesis pae00524
Galactose metabolism pae00052
Glutathione metabolism pae00480
Glycolysis / Gluconeogenesis pae00010
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Pentose phosphate pathway pae00030
Purine metabolism pae00230
Starch and sucrose metabolism pae00500
Streptomycin biosynthesis pae00521

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-000b-1932000000-59f4881b86595037d013	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-0f7t-1933000000-4894135f21c21c369428	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX)	splash10-00di-9522000000-81266970683faa1f2aaf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX)	splash10-00di-9412000000-2f2a0e772025b48bf6f3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-000j-1956000000-692b4df2b9c16f6a780c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-000i-1957000000-bd94955ffc1474153a48	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0v0a-0596000000-676527ddfc1d596e78f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03di-0090000000-5653def80d1b5ff0eebb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000b-9200000000-66741d773ac31b347625	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000t-9000000000-068809fcfaff0d387e6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-1090000000-d6e539d78b38c01dafea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-9210000000-8b9ff1c5095f48a81fef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9000000000-f6e1147852f75db4c0a4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-002b-9000000000-1c52fd659f8a2b795e51	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-d3f6a05e18ea6d56c56d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-0890000000-5f3047c92c970dfe6927	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-004i-0900000000-b84eb7685667fa7ee85e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-004i-2900000000-d4a0d51bb6e2da28533a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-6900000000-dfb5bcbd9a7439c32352	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03gi-9600000000-a0922c82e185f6b5aa67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0006-0290000000-7ac7b397c52f29cd3822	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-052b-6590000000-5cdbc23378480ac55c4f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-1900000000-b74270f21c6086362227	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9000000000-bc69e8fa215a3b82dcf2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Benkoel L, Chamlian A, Barrat E, Laffargue P: The use of ferricyanide for the electron microscopic demonstration of dehydrogenases in human steroidogenic cells. J Histochem Cytochem. 1976 Nov;24(11):1194-203. Pubmed: 1002973
Boden G, Chen X, Ruiz J, White JV, Rossetti L: Mechanisms of fatty acid-induced inhibition of glucose uptake. J Clin Invest. 1994 Jun;93(6):2438-46. Pubmed: 8200979
Boden G, Jadali F, White J, Liang Y, Mozzoli M, Chen X, Coleman E, Smith C: Effects of fat on insulin-stimulated carbohydrate metabolism in normal men. J Clin Invest. 1991 Sep;88(3):960-6. Pubmed: 1885781
Brehm A, Krssak M, Schmid AI, Nowotny P, Waldhausl W, Roden M: Increased lipid availability impairs insulin-stimulated ATP synthesis in human skeletal muscle. Diabetes. 2006 Jan;55(1):136-40. Pubmed: 16380486
Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. Pubmed: 11488613
Chang PY, Jensen J, Printz RL, Granner DK, Ivy JL, Moller DE: Overexpression of hexokinase II in transgenic mice. Evidence that increased phosphorylation augments muscle glucose uptake. J Biol Chem. 1996 Jun 21;271(25):14834-9. Pubmed: 8662926
Cigolini M, Bonora E, Querena M, Moghetti P, Cacciatori V, Zancanaro C, Benati D, Muggeo M: Differences in glucose metabolic enzyme activities in human adipose tissue from abdominal and gluteal regions. Metabolism. 1988 Sep;37(9):820-3. Pubmed: 3419322
Cline GW, Petersen KF, Krssak M, Shen J, Hundal RS, Trajanoski Z, Inzucchi S, Dresner A, Rothman DL, Shulman GI: Impaired glucose transport as a cause of decreased insulin-stimulated muscle glycogen synthesis in type 2 diabetes. N Engl J Med. 1999 Jul 22;341(4):240-6. Pubmed: 10413736
Fortpied J, Maliekal P, Vertommen D, Van Schaftingen E: Magnesium-dependent phosphatase-1 is a protein-fructosamine-6-phosphatase potentially involved in glycation repair. J Biol Chem. 2006 Jul 7;281(27):18378-85. Epub 2006 May 1. Pubmed: 16670083
Foster JD, Pederson BA, Nordlie RC: Glucose-6-phosphatase structure, regulation, and function: an update. Proc Soc Exp Biol Med. 1997 Sep;215(4):314-32. Pubmed: 9270716
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Lehto M, Xiang K, Stoffel M, Espinosa R 3rd, Groop LC, Le Beau MM, Bell GI: Human hexokinase II: localization of the polymorphic gene to chromosome 2. Diabetologia. 1993 Dec;36(12):1299-302. Pubmed: 8307259
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
Petersen KF, Hendler R, Price T, Perseghin G, Rothman DL, Held N, Amatruda JM, Shulman GI: 13C/31P NMR studies on the mechanism of insulin resistance in obesity. Diabetes. 1998 Mar;47(3):381-6. Pubmed: 9519743
Price TB, Laurent D, Petersen KF: 13C/31P NMR studies on the role of glucose transport/phosphorylation in human glycogen supercompensation. Int J Sports Med. 2003 May;24(4):238-44. Pubmed: 12784164
Roden M: How free fatty acids inhibit glucose utilization in human skeletal muscle. News Physiol Sci. 2004 Jun;19:92-6. Pubmed: 15143200
Roussel R, Carlier PG, Wary C, Velho G, Bloch G: Evidence for 100% 13C NMR visibility of glucose in human skeletal muscle. Magn Reson Med. 1997 Jun;37(6):821-4. Pubmed: 9178231
Schalin-Jantti C, Harkonen M, Groop LC: Impaired activation of glycogen synthase in people at increased risk for developing NIDDM. Diabetes. 1992 May;41(5):598-604. Pubmed: 1568529
Turvey EA, Heigenhauser GJ, Parolin M, Peters SJ: Elevated n-3 fatty acids in a high-fat diet attenuate the increase in PDH kinase activity but not PDH activity in human skeletal muscle. J Appl Physiol. 2005 Jan;98(1):350-5. Pubmed: 15591305
Vaag A, Damsbo P, Hother-Nielsen O, Beck-Nielsen H: Hyperglycaemia compensates for the defects in insulin-mediated glucose metabolism and in the activation of glycogen synthase in the skeletal muscle of patients with type 2 (non-insulin-dependent) diabetes mellitus. Diabetologia. 1992 Jan;35(1):80-8. Pubmed: 1541385
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Vestergaard H, Bjorbaek C, Hansen T, Larsen FS, Granner DK, Pedersen O: Impaired activity and gene expression of hexokinase II in muscle from non-insulin-dependent diabetes mellitus patients. J Clin Invest. 1995 Dec;96(6):2639-45. Pubmed: 8675629
Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
Villar-Palasi C, Guinovart JJ: The role of glucose 6-phosphate in the control of glycogen synthase. FASEB J. 1997 Jun;11(7):544-58. Pubmed: 9212078

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17665
HMDB ID	HMDB01401
Pubchem Compound ID	439284
Kegg ID	C00092
ChemSpider ID	5743
Wikipedia	Glucose 6-phosphate
BioCyc ID	GLC-6-P
EcoCyc ID	GLC-6-P

Enzymes

Protein Details

• Glucose-6-phosphate isomerase

General function:: Involved in glucose-6-phosphate isomerase activity
Specific function:: D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:: pgi
Locus Tag:: PA4732
Molecular weight:: 61.9 kDa

Reactions

D-glucose 6-phosphate = D-fructose 6-phosphate.

Protein Details

• Glucokinase

General function:: Involved in glucokinase activity
Specific function:: Not highly important in Pseudomonas aeruginosa as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
Gene Name:: glk
Locus Tag:: PA3193
Molecular weight:: 34.6 kDa

Reactions

ATP + D-glucose = ADP + D-glucose 6-phosphate.

Protein Details

• Glucose-6-phosphate 1-dehydrogenase

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
Locus Tag:: PA3183
Molecular weight:: 55.6 kDa

Reactions

D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH.

Protein Details

• Phosphoglucomutase

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:: pgm
Locus Tag:: PA5131
Molecular weight:: 55.6 kDa

Reactions

Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate.

Glucose 6-phosphate (PAMDB000372)

Structure for Glucose 6-phosphate (PAMDB000372)

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters