P. aeruginosa Metabolome Database: Fructose 6-phosphate (PAMDB000047)

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

PAMDB000047

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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

β-D-fructofuranose 6-phosphate
β-D-fructofuranose 6-phosphoric acid
A-D-Fructose-6-P
b-D-Fructofuranose 6-phosphate
b-D-Fructofuranose 6-phosphoric acid
Beta-D-Fructofuranose 6-phosphate
beta-D-Fructofuranose 6-phosphoric acid
D-Fructofuranose 6-phosphate
D-Fructofuranose 6-phosphoric acid
D-Fructose 6-phosphate
D-Fructose 6-phosphorate
D-Fructose 6-phosphoric acid
D-Fructose-6-P
D-Fructose-6-phosphate
D-Fructose-6-phosphoric acid
F6P
FPC
Fru-6-P
Fruc6p
Fructose 6-phosphate
Fructose 6-phosphoric acid
Fructose-6-P
Fructose-6-phosphate
Fructose-6-phosphoric acid
Fructose-6P
Neuberg ester
β-D-Fructofuranose 6-phosphate
β-D-Fructofuranose 6-phosphoric acid

Chemical Formula:

C₆H₁₃O₉P

Average Molecular Weight:

260.1358

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Organic phosphate
Monosaccharide
Beta-hydroxy ketone
Beta-ketoaldehyde
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Polyol
Ketone
1,2-diol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-fructose 6-phosphate (CHEBI:15946 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	911 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	23.2 mg/mL	ALOGPS
logP	-1.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	48.43 m³·mol^-1	ChemAxon
Polarizability	20.87 Å³	ChemAxon
Number of Rings	0	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:

More...

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Amino sugar and nucleotide sugar metabolism pae00520
Carbon fixation in photosynthetic organisms pae00710
Fructose and mannose metabolism pae00051
Galactose metabolism pae00052
Glycolysis / Gluconeogenesis pae00010
Lipopolysaccharide biosynthesis pae00540
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Pentose and glucuronate interconversions pae00040
Pentose phosphate pathway pae00030
Starch and sucrose metabolism pae00500

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)	splash10-0gba-1943000000-9b9bb3f9964b519fa26b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-014j-1943000000-0be5d726668730e99be0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-014j-1954000000-9fa83268db2925e9478d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-000b-0934000000-eb61ccae8d0b23564bc7	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-000b-0934000000-c2a49f4f2d11d3e60a9e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-000j-0925000000-a6b6a121cb447c890019	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0f7a-1934000000-b28e738e5093324060d9	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-014i-3966000000-fee84a4ec7828d92e8b6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-014i-1955000000-32da70382eccbcbbb574	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0229-5090000000-281699f4bce06db0b1b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006x-9730000000-b72576e6bb1ae73e6881	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0kbf-9740000000-130bb715a91e870b5480	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0aor-0690000000-b640c7fba12f06d6bfa2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00kb-9710000000-5d6429381cefb6a2bdc7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9100000000-51c3f5ca7ef3f190f1df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-054k-9000000000-75c50b162633f723546d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-07895e6c6f3e4a816391	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	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:

Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95. Pubmed: 9451038
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
Gagnon M, Kheadr EE, Le Blay G, Fliss I: In vitro inhibition of Escherichia coli O157:H7 by bifidobacterial strains of human origin. Int J Food Microbiol. 2004 Apr 1;92(1):69-78. Pubmed: 15033269
Gapparov MM, Virovets OA: [Nonenzymatic glycosylation of serum albumin and thymic DNA by food monosugars and their natural metabolites that form in the body] Vopr Pitan. 1990 Jan-Feb;(1):36-40. Pubmed: 2346009
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
Karlander S, Roovete A, Vranic M, Efendic S: Glucose and fructose 6-phosphate cycle in humans. Am J Physiol. 1986 Nov;251(5 Pt 1):E530-6. Pubmed: 3777162
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
Markuszewski MJ, Szczykowska M, Siluk D, Kaliszan R: Human red blood cells targeted metabolome analysis of glycolysis cycle metabolites by capillary electrophoresis using an indirect photometric detection method. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):636-42. Pubmed: 15925468
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
Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. Pubmed: 1332571
Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. Pubmed: 16077128
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
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
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
Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. Pubmed: 16055050
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	15946
HMDB ID	HMDB00124
Pubchem Compound ID	69507
Kegg ID	C00085
ChemSpider ID	62713
Wikipedia	Fructose 6-phosphate
BioCyc ID	FRUCTOSE-6P
EcoCyc ID	FRUCTOSE-6P
Ligand Expo	F6R

Enzymes

Protein Details

• Mannitol-1-phosphate 5-dehydrogenase

General function:: Involved in oxidation-reduction process
Specific function:: D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:: mtlD
Locus Tag:: PA2342
Molecular weight:: 54.3 kDa

Reactions

D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH.

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

• Transaldolase B

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: talB
Locus Tag:: PA2796
Molecular weight:: 33.9 kDa

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate.

Protein Details

• Fructose-1,6-bisphosphatase class 1

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
Locus Tag:: PA5110
Molecular weight:: 37.2 kDa

Reactions

D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.

Protein Details

• Glucosamine--fructose-6-phosphate aminotransferase [isomerizing]

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
Locus Tag:: PA5549
Molecular weight:: 66.3 kDa

Reactions

L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate.

Protein Details

• Transketolase 1

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
Locus Tag:: PA0548
Molecular weight:: 72.2 kDa

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.

Protein Details

• deacetylase of acs and cheY, regulates chemotaxis

General function:: Not Available
Specific function:: Not Available
Gene Name:: cobB
Locus Tag:: PA1273
Molecular weight:: 46.5 kDa

Fructose 6-phosphate (PAMDB000047)

Structure for Fructose 6-phosphate (PAMDB000047)

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters