P. aeruginosa Metabolome Database: Fructose 1,6-bisphosphate (PAMDB000236)

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

PAMDB000236

Identification

Name:

Fructose 1,6-bisphosphate

Description:

The hydrolysis of fructose 1,6-bisphosphate is catalized by Fructose-1,6-bisphosphatase (fru-1,6-P2ase, EC 3.1.3.11) to fructose 6-phosphate and inorganic phosphate and provides a mechanism to permit the reversal of the glycolysis reaction (catalyzed by 6-phosphofructo-1-kinase).(OMIM)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

β-D-fructose-1,6-diphosphate
β-D-fructose-1,6-diphosphoric acid
b-D-Fructose-1,6-diphosphate
b-D-Fructose-1,6-diphosphoric acid
Beta-D-Fructose-1,6-diphosphate
beta-D-Fructose-1,6-diphosphoric acid
D-Fructose 1,6-biphosphate
D-Fructose 1,6-biphosphoric acid
D-Fructose 1,6-bis(dihydrogen phosphate)
D-Fructose 1,6-bis(dihydrogen phosphoric acid)
D-Fructose 1,6-bisphosphate
D-Fructose 1,6-bisphosphoric acid
D-Fructose 1,6-diphosphate
D-Fructose 1,6-diphosphoric acid
D-Fructose-1,6-bisphosphate
D-Fructose-1,6-bisphosphoric acid
D-Fructose-1,6-diphosphate
D-Fructose-1,6-diphosphoric acid
Diphosphofructose
Esafosfan
Esafosfina
F1,6P
FBP
FDP
Fosfructose
Fructose 1,6-bis
Fructose 1,6-bisphosphate
Fructose 1,6-bisphosphoric acid
Fructose 1,6-diphosphate
Fructose 1,6-diphosphoric acid
Fructose-1,6-biphosphate
Fructose-1,6-biphosphoric acid
Fructose-1,6-diphosphate
Fructose-1,6-diphosphoric acid
Harden-Young ester
β-D-Fructose-1,6-diphosphate
β-D-Fructose-1,6-diphosphoric acid

Chemical Formula:

C₆H₁₄O₁₂P₂

Average Molecular Weight:

340.1157

Monoisotopic Molecular Weight:

339.996048936

InChI Key:

RNBGYGVWRKECFJ-ZXXMMSQZSA-N

InChI:

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

CAS number:

488-69-7

IUPAC Name:

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

Traditional IUPAC Name:

[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Oxolane
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	94 mg/mL [sodium salt, HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	16.0 mg/mL	ALOGPS
logP	-1.5	ALOGPS
logP	-2.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.93	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.64 m³·mol^-1	ChemAxon
Polarizability	24.91 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:

β-D-fructofuranose 1-phosphate + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP + Fructose 1,6-bisphosphate

More...

Pathways:

Carbon fixation in photosynthetic organisms pae00710
Fructose and mannose metabolism pae00051
Galactose metabolism pae00052
Glycolysis / Gluconeogenesis pae00010
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Pentose phosphate pathway pae00030
Starch and sucrose metabolism pae00500

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0092-0249000000-eb939046a288ed654b99	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-5576a6262edb99fd1ef1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0900000000-5576a6262edb99fd1ef1	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,13C] 2D NMR Spectrum	Not Available

References

References:

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
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:

Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16905
HMDB ID	HMDB01058
Pubchem Compound ID	718
Kegg ID	C00354
ChemSpider ID	393163
Wikipedia	Fructose 1,6-diphosphate
BioCyc ID	FRUCTOSE-16-DIPHOSPHATE
EcoCyc ID	FRUCTOSE-16-DIPHOSPHATE
Ligand Expo	AHG

Enzymes

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

• 1-phosphofructokinase

General function:: Involved in 1-phosphofructokinase activity
Specific function:: ATP + D-fructose 1-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:: fruK
Locus Tag:: PA3561
Molecular weight:: 33.4 kDa

Reactions

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

Fructose 1,6-bisphosphate (PAMDB000236)

Structure for Fructose 1,6-bisphosphate (PAMDB000236)

Enzymes

Reactions

Reactions