Fructose 6-phosphate (YMDB00078)

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Identification

YMDB ID

YMDB00078

Name

Fructose 6-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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 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

MOL SDF PDB SMILES InChI

Synonyms

D-Fructose 6-phosphate
D-Fructose 6-phosphorate
D-Fructose 6-phosphoric acid
D-fructose-6-P
D-fructose-6-phosphate
FPC
fru-6-P
Fructose 6-phosphate
Fructose 6-phosphic acid
fructose-6-P
Fructose-6-phosphate
fructose-6P
Neuberg ester
Fructose-6-phosphoric acid
Fructose 6-phosphoric acid
Fructose-6-phosphate, (alpha-D)-isomer
Fructose-6-phosphate, (beta-D)-isomer
Fructose-6-phosphate, disodium salt, (D)-isomer
Fructose-6-phosphate, (D)-isomer
Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomer
Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomer
Fructose-6-phosphate, barium (1:1) salt, (D)-isomer
Fructose-6-phosphate, barium salt, (D)-isomer
Fructose-6-phosphate, sodium salt, (D)-isomer
Fructose-6-phosphate, calcium salt, (D)-isomer
Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomer
Fructose-6-phosphate, sodium salt

CAS number

643-13-0

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

IUPAC Name

{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid

Traditional IUPAC Name

D-fructose 6-phosphate

Chemical Formula

C₆H₁₃O₉P

SMILES

[H]OC([H])([H])C(=O)[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]

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

Hexose phosphate
Monosaccharide phosphate
Monoalkyl phosphate
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-fructose 6-phosphate (CHEBI:15946 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	911 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	23.2 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.4	ChemAxon
logS	-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	20.78 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

Organoleptic Properties

Not Available

SMPDB Pathways

Amino sugar and nucleotide sugar metabolism	PW002413
Ethanol fermentation	PW002448
Glycolysis I	PW002386

KEGG Pathways

Amino sugar and nucleotide sugar metabolism

ec00520

SMPDB Reactions

Fructose 6-phosphate ↔ Glucose 6-phosphate

Beta-D-Glucose 6-phosphate ↔ Fructose 6-phosphate

Fructose 6-phosphate → Beta-D-Glucose 6-phosphate

Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADP

KEGG Reactions

Adenosine triphosphate + Fructose 6-phosphate → D-Fructose 2,6-bisphosphate + hydron + ADP

D-Fructose 2,6-bisphosphate + water → Fructose 6-phosphate + phosphate

water + Fructose 1,6-bisphosphate → Fructose 6-phosphate + phosphate

water + Glucosamine 6-phosphate → Fructose 6-phosphate + Ammonium

Beta-D-Glucose 6-phosphate ↔ Fructose 6-phosphate

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
400 ± 30 µM	20 ml 2% (wt/vol) glucose, 0.5% (wt/vol) ammonium sulfate, 0.17% (wt/vol) yeast nitrogen base without amino acids (Difco, Detroit, MI) and 100 mM potassium phthalate at pH 5.0, supplemented with required nutrients (40 mg/L uracil, 40 mg/L Ltryptophan, 60	aerobic	Baker's yeast	PMID: 11135551
650 ± 30 µM	Synthetic medium with 2% glucose	aerobic;growing cells	Baker's yeast	PMID: 6229402
94 ± 13 µM	Synthetic medium with 2% glucose	aerobic;resting cells	Baker's yeast	PMID: 6229402
90 ± 30 µM	Synthetic medium with 2% glucose	anaerobic;resting cells	Baker's yeast	PMID: 6229402
120 ± 50 µM	Synthetic medium with 2% galactose	aerobic;resting cells	Baker's yeast	PMID: 6229402
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-0gba-1943000000-9b9bb3f9964b519fa26b	JSpectraViewer \| 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	JSpectraViewer \| 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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000b-0934000000-eb61ccae8d0b23564bc7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000b-0934000000-c2a49f4f2d11d3e60a9e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000j-0925000000-a6b6a121cb447c890019	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f7a-1934000000-b28e738e5093324060d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-014i-3966000000-fee84a4ec7828d92e8b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)	splash10-014i-1955000000-32da70382eccbcbbb574	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-1943000000-9b9bb3f9964b519fa26b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014j-1943000000-0be5d726668730e99be0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014j-1954000000-9fa83268db2925e9478d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000b-0934000000-eb61ccae8d0b23564bc7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000b-0934000000-c2a49f4f2d11d3e60a9e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000j-0925000000-a6b6a121cb447c890019	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f7a-1934000000-b28e738e5093324060d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3966000000-fee84a4ec7828d92e8b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1955000000-32da70382eccbcbbb574	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-1933000000-1c8febd80da1382bec31	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k97-9840000000-4f9f16f21249d9870dfa	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00o9-7934540000-e23e661c1babf5e063a8	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0229-5090000000-281699f4bce06db0b1b0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006x-9730000000-b72576e6bb1ae73e6881	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0kbf-9740000000-130bb715a91e870b5480	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0aor-0690000000-b640c7fba12f06d6bfa2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00kb-9710000000-5d6429381cefb6a2bdc7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9100000000-51c3f5ca7ef3f190f1df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-054k-9000000000-75c50b162633f723546d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-07895e6c6f3e4a816391	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0aor-0690000000-b640c7fba12f06d6bfa2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-f31b175fc6a9941a2451	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9220000000-962294aed3032864dc90	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-c2dc78595233b4d4df78	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-3590000000-3fc4dac2f46082421870	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0c04-9610000000-77e7a6ced5ab4dda6f86	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-e4500e644878a4632447	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ar9-9720000000-7ca18e5a32ef069ff21a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-00032f32c05509571a9f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5e859d2084880df68725	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-9620000000-1a2150ea2d68dcce9b24	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9000000000-f2969657deda9ac99077	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d5aaca13a836cb9f1725	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dm-2980000000-ccecfa1c0258f9267846	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-550809f9719b91a7807a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-501178ab2f5d5affab48	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Raamsdonk, L. M., Teusink, B., Broadhurst, D., Zhang, N., Hayes, A., Walsh, M. C., Berden, J. A., Brindle, K. M., Kell, D. B., Rowland, J. J., Westerhoff, H. V., van Dam, K., Oliver, S. G. (2001). "A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations." Nat Biotechnol 19:45-50.11135551
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
Fonzi, W. A., Shanley, M., Opheim, D. J. (1979). "Relationship of glycolytic intermediates, glycolytic enzymes, and ammonia to glycogen metabolism during sporulation in the yeast Saccharomyces cerevisiae." J Bacteriol 137:285-294.368017
Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
Heinisch, J. (1986). "Isolation and characterization of the two structural genes coding for phosphofructokinase in yeast." Mol Gen Genet 202:75-82.3007939
Banki, K., Halladay, D., Perl, A. (1994). "Cloning and expression of the human gene for transaldolase. A novel highly repetitive element constitutes an integral part of the coding sequence." J Biol Chem 269:2847-2851.8300619
Watzele, G., Tanner, W. (1989). "Cloning of the glutamine:fructose-6-phosphate amidotransferase gene from yeast. Pheromonal regulation of its transcription." J Biol Chem 264:8753-8758.2656689
Boles, E., Zimmermann, F. K. (1993). "Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster." Curr Genet 23:187-191.8435847
Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15946
HMDB ID	HMDB00124
Pubchem Compound ID	69507
Kegg ID	C00085
ChemSpider ID	62713
FOODB ID	FDB021896
Wikipedia	Fructose_6-phosphate
BioCyc ID	FRUCTOSE-6P

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

Structure for #<Compound:0xb0b0af94>

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