D-Fructose 2,6-bisphosphate (YMDB00011)

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Identification

YMDB ID

YMDB00011

Name

D-Fructose 2,6-bisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Fructose 2,6-bisphosphate, also known as phosphofructokinase activator, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Fructose 2,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. Within yeast, D-fructose 2,6-bisphosphate participates in a number of enzymatic reactions. In particular, D-fructose 2,6-bisphosphate can be biosynthesized from β-D-fructofuranose 6-phosphate through its interaction with the enzyme 6-phosphofructose-2-kinase. In addition, D-fructose 2,6-bisphosphate can be converted into β-D-fructofuranose 6-phosphate through the action of the enzyme fructose-2,6-bisphosphatase. In yeast, D-fructose 2,6-bisphosphate is involved in the metabolic pathway called the fructose metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2,6-Di-O-phosphono-b-D-fructofuranose
2,6-Di-O-phosphono-beta-D-fructofuranose
2,6-Di-O-phosphono-β-D-fructofuranose
b-D-fructose 2,6-bisphosphate
beta-D-fructose 2,6-bisphosphate
D-Fructose 2,6-bisphosphate
D-Fructose 2,6-bisphosphic acid
D-Fructose 2,6-bisphosphoric acid
Fru 2,6-P2, Fructose 2,6-diphosphate
Fructose 2,6-biphosphate
fructose 2,6-bisphosphate
Fructose 2,6-diphosphate
Phosphofructokinase activation factor
Phosphofructokinase activator
Fructose-2,6-diphosphate
D-Fructose 2,6-diphosphate
beta-D-Fructose 2,6-diphosphate
β-D-Fructose 2,6-diphosphate

CAS number

Not Available

Weight

Average: 340.1157
Monoisotopic: 339.996048936

InChI Key

YXWOAJXNVLXPMU-ZXXMMSQZSA-N

InChI

InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

IUPAC Name

{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

Traditional IUPAC Name

fructose-2,6-diphosphate

Chemical Formula

C₆H₁₄O₁₂P₂

SMILES

[H]OC([H])([H])[C@@]1(OP(=O)(O[H])O[H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose 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

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Alkyl phosphate
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 2,6-bisphosphate (CHEBI:28602 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	15.8 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.68	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	58.11 m³·mol⁻¹	ChemAxon
Polarizability	25.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	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

Fructose Metabolism

PW002390

KEGG Pathways

Fructose and mannose metabolism

ec00051

SMPDB Reactions

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

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

KEGG Reactions

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

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

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1200 ± 200 µM	Synthetic medium with 2% glucose	aerobic;growing cells	Baker's yeast	PMID: 6229402
360 ± 1 µM	Synthetic medium with 2% glucose	aerobic;resting cells	Baker's yeast	PMID: 6229402
510 ± 20 µM	Synthetic medium with 2% glucose	anaerobic;resting cells	Baker's yeast	PMID: 6229402
1700 ± 200 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 (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9512000000-82418e0e398490357c5e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2190010000-53cf738181713979e181	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, negative	splash10-000i-0019000000-7b58b1d6169f22e732a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, negative	splash10-000m-2496000000-40ad2c4944ae5c0701f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, negative	splash10-0002-9830000000-a9cbb8a3dba391a8858b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, negative	splash10-002b-9200000000-6dcaff4e5eee3799656f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, negative	splash10-004j-9100000000-9851b59e56acb7c5802c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-3797000000-cb11e27ce8d0be902a39	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9132000000-b908246df46f54e31180	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dm-9600000000-19262e5981934144e1aa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7409000000-0240bd8771cde252759c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-8930f98e412f1b68e30b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fb204edc71835bcbaaad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0393000000-f7f716e45f745f0bec68	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1920000000-f0eccbb835449758a67c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9410000000-f9f76bd919e86701aaff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9008000000-d519306c146482d051d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9001000000-2d0e9375a49babbe9d93	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-bc05f33d90e2bf18235c	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C 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
1D NMR	1H 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
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
Francois, J., Van Schaftigen, E., Hers, H. G. (1988). "Characterization of phosphofructokinase 2 and of enzymes involved in the degradation of fructose 2,6-bisphosphate in yeast." Eur J Biochem 171:599-608.2831055
Kretschmer, M., Schellenberger, W., Otto, A., Kessler, R., Hofmann, E. (1987). "Fructose-2,6-bisphosphatase and 6-phosphofructo-2-kinase are separable in yeast." Biochem J 246:755-759.2825652
Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
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:

Shulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.

External Links:

Resource	Link
CHEBI ID	28602
HMDB ID	HMDB01047
Pubchem Compound ID	105021
Kegg ID	C00665
ChemSpider ID	24534245
FOODB ID	FDB022390
Wikipedia	Fructose_2,6-bisphosphate
BioCyc ID	CPD-535

Enzymes

Protein Details

1. Fructose-2,6-bisphosphatase

General function:: Involved in catalytic activity
Specific function:: This is predominantly if not solely a fructose-2,6- bisphosphatase
Gene Name:: FBP26
Uniprot ID:: P32604
Molecular weight:: 52594.5

Reactions

Beta-D-fructose 2,6-bisphosphate + H(2)O → D-fructose 6-phosphate + phosphate.

Protein Details

2. 6-phosphofructo-2-kinase 2

General function:: Involved in catalytic activity
Specific function:: Synthesis of fructose 2,6-bisphosphate
Gene Name:: PFK27
Uniprot ID:: Q12471
Molecular weight:: 45317.10156

Reactions

ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.

Protein Details

3. Putative 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase YLR345W

General function:: Involved in catalytic activity
Specific function:: Synthesis and degradation of fructose 2,6-bisphosphate
Gene Name:: Not Available
Uniprot ID:: Q06137
Molecular weight:: 58385.19922

Reactions

Beta-D-fructose 2,6-bisphosphate + H(2)O → D-fructose 6-phosphate + phosphate.
ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.

Protein Details

4. 6-phosphofructo-2-kinase 1

General function:: Involved in catalytic activity
Specific function:: Synthesis of fructose 2,6-bisphosphate
Gene Name:: PFK26
Uniprot ID:: P40433
Molecular weight:: 93416.20313

Reactions

ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.

Protein Details

5. Repressible alkaline phosphatase

General function:: Involved in catalytic activity
Specific function:: A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:: PHO8
Uniprot ID:: P11491
Molecular weight:: 63003.60156

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.
(2E,6E)-farnesyl diphosphate + H(2)O → (2E,6E)-farnesol + diphosphate.
beta-D-fructose 2,6-bisphosphate + H2O → beta-D-fructofuranose 2-phosphate + phosphate

Structure for #<Compound:0xaa70d35c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions