ECMDB: beta-D-Fructose 6-phosphate (ECMDB03971) (M2MDB000547)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (14)XML

Proteins (3631)

Record Information

Version

2.0

Creation Date

2012-05-31 14:01:34 -0600

Update Date

2015-06-03 15:54:35 -0600

Secondary Accession Numbers

ECMDB03971

Identification

Name:

beta-D-Fructose 6-phosphate

Description

Beta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase and Transaldolase.

Structure

MOL SDF PDB SMILES InChI

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
b-D-Fructose 6-phosphate
b-D-Fructose 6-phosphoric acid
Beta-D-Fructofuranose 6-phosphate
beta-D-Fructofuranose 6-phosphoric acid
Beta-D-Fructose 6-phosphate
beta-D-Fructose 6-phosphoric acid
D-Fructofuranose 6-phosphate
D-Fructofuranose 6-phosphoric acid
D-Fructose-6-P
D-Fructose-6-phosphate
D-Fructose-6-phosphoric acid
F6P
Fru-6-P
Fruc6p
Fructose-6-P
Fructose-6-phosphate
Fructose-6-phosphoric acid
Fructose-6P
β-D-Fructofuranose 6-phosphate
β-D-Fructofuranose 6-phosphoric acid
β-D-Fructose 6-phosphate
β-D-Fructose 6-phosphoric acid

Chemical Formula:

C₆H₁₃O₉P

Weight:

Average: 260.1358
Monoisotopic: 260.029718526

InChI Key:

BGWGXPAPYGQALX-ARQDHWQXSA-N

InChI:

InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

β-D-fructofuranose 6-phosphate

SMILES:

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

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
Hemiacetal
Polyol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 6-phosphate (CHEBI:16084 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	33.4 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.9	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.5	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	4	ChemAxon
Refractivity	47.23 m³·mol⁻¹	ChemAxon
Polarizability	20.92 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:

SMPDB Pathways:

D-sorbitol degradation II	PW002022
Pentose Phosphate	PW000893
Starch and sucrose metabolism	PW000941
colanic acid building blocks biosynthesis	PW000951

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Fructose and mannose metabolism ec00051
Glycolysis / Gluconeogenesis ec00010
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

N-acetylglucosamine degradation I GLUAMCAT-PWY
D-allose degradation PWY0-44
D-mannose degradation MANNCAT-PWY
GDP-mannose biosynthesis PWY-5659
UDP-N-acetyl-D-glucosamine biosynthesis I UDPNAGSYN-PWY
gluconeogenesis I GLUCONEO-PWY
glycolysis I GLYCOLYSIS
mannitol degradation I MANNIDEG-PWY
pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY
sorbitol degradation II SORBDEG-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
55± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9422000000-bee9b5c8192cd70afd4b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9422000000-bee9b5c8192cd70afd4b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9330000000-5c27e76b48f712dafdf1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0540-8097650000-bd7cf45abb555a5c08da	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9200000000-890d2bc5c099d333bb87	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0090000000-9e5a9a987b6541abb2c7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0ab9-0000509000-ba24f5137a9692d147ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2980000000-6b021fc643037857d79c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-6950000000-9aeea6f58646b1ddfd2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-9300000000-163fede30ff57a757356	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-7390000000-3b9471399e651e34edcb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-107d49541ec3b4b1213f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9182363b16cd6b3e720b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3090000000-7ae40fd439a28bd2393e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-53fac253975be4bb66f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-1790000000-cf4773c8e21b0c55570e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9810000000-21980e2a6a612b295b9d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-a08dc200cb22f420d5bc	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16084
HMDB ID	HMDB03971
Pubchem Compound ID	440641
Kegg ID	C05345
ChemSpider ID	389526
Wikipedia ID	Fructose_6-phosphate
BioCyc ID	FRUCTOSE-6P
EcoCyc ID	FRUCTOSE-6P
Ligand Expo	F6P

Enzymes

Protein Details

1. Mannose-6-phosphate isomerase

General function:: Involved in mannose-6-phosphate isomerase activity
Specific function:: Involved in the conversion of glucose to GDP-L-fucose, which can be converted to L-fucose, a capsular polysaccharide
Gene Name:: manA
Uniprot ID:: P00946
Molecular weight:: 42850

Reactions

D-mannose 6-phosphate = D-fructose 6-phosphate.

Protein Details

2. Sorbitol-6-phosphate 2-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:: srlD
Uniprot ID:: P05707
Molecular weight:: 27858

Reactions

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

Protein Details

3. 6-phosphofructokinase isozyme 2

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:: pfkB
Uniprot ID:: P06999
Molecular weight:: 32456

Reactions

ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.

Protein Details

4. 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
Uniprot ID:: P09424
Molecular weight:: 41139

Reactions

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

Protein Details

5. 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
Uniprot ID:: P0A6T1
Molecular weight:: 61529

Reactions

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

Protein Details

6. 6-phosphofructokinase isozyme 1

General function:: Involved in ATP binding
Specific function:: ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:: pfkA
Uniprot ID:: P0A796
Molecular weight:: 34842

Reactions

ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.

Protein Details

7. Transaldolase A

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: talA
Uniprot ID:: P0A867
Molecular weight:: 35659

Reactions

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

Protein Details

8. 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
Uniprot ID:: P0A870
Molecular weight:: 35219

Reactions

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

Protein Details

9. 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
Uniprot ID:: P0A993
Molecular weight:: 36834

Reactions

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

Protein Details

10. Fructose-1,6-bisphosphatase class 2

General function:: Involved in glycerol metabolic process
Specific function:: D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:: glpX
Uniprot ID:: P0A9C9
Molecular weight:: 35852

Reactions

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

Protein Details

11. Fructokinase

General function:: Transcription
Specific function:: Catalyzes the phosphorylation of fructose to fructose-6- P. Has also low level glucokinase activity in vitro. Is not able to phosphorylate D-ribose, D-mannitol, D-sorbitol, inositol, and L-threonine
Gene Name:: mak
Uniprot ID:: P23917
Molecular weight:: 32500

Reactions

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

Protein Details

12. 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
Uniprot ID:: P27302
Molecular weight:: 72211

Reactions

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

Protein Details

13. D-allulose-6-phosphate 3-epimerase

General function:: Involved in catalytic activity
Specific function:: Specific function unknown
Gene Name:: alsE
Uniprot ID:: P32719
Molecular weight:: 26109

Protein Details

14. Transketolase 2

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:: tktB
Uniprot ID:: P33570
Molecular weight:: 73042

Reactions

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

beta-D-Fructose 6-phosphate (ECMDB03971) (M2MDB000547)

Structure for #<Compound:0xadfb3760>

Enzymes

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