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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:24 UTC
HMDB IDHMDB0000124
Secondary Accession Numbers
  • HMDB00124
Metabolite Identification
Common NameFructose 6-phosphate
DescriptionFructose 6-phosphate (F6P) 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. F6P is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. Fructose 6-phosphate is a fundamental metabolite and exists in all living species, ranging from bacteria to plants to humans. The great majority of glucose is converted to fructose 6-phosphate as part of the glycolytic metabolic pathway (glycolysis). Specifically, F6P is produce is produced by the isomerisation of glucose 6-phosphate via the enzyme phosphoglucose isomerase. F6P is in turn further phosphorylated to fructose-1,6-bisphosphate by the enzyme phosphofructokinase-1. Glycolysis is the metabolic pathway that converts glucose into pyruvic acid. The free energy released in this process is used to form ATP and reduced nicotinamide adenine dinucleotide (NADH). In addition to its key involvement in glycolysis, fructose 6-phosphate can also be biosynthesized from glucosamine 6-phosphate via the enzyme glucosamine-6-phosphate isomerase 1. In addition, fructose 6-phosphate and L-glutamine can be converted into glucosamine 6-phosphate and L-glutamic acid through the action of the enzyme glutamine--fructose-6-phosphate aminotransferase.
Structure
Thumb
Synonyms
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional NameD-fructose 6-phosphate
CAS Registry Number643-13-0
SMILES
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
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
InChI KeyGSXOAOHZAIYLCY-HSUXUTPPSA-N
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility911 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_test_neg141.430932474
[M-H]-Astarita_neg142.730932474
[M-H]-Baker148.02530932474
[M-H]-Not Available141.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000407
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Locations
  • Intestine
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.01 +/- 0.47 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified1.46 +/- 0.81 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified1.57 +/- 1.71 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDDB04493
Phenol Explorer Compound IDNot Available
FooDB IDFDB021896
KNApSAcK IDNot Available
Chemspider ID62713
KEGG Compound IDC00085
BioCyc IDCPD-15709
BiGG ID33795
Wikipedia LinkFructose 6-phosphate
METLIN ID5159
PubChem Compound69507
PDB IDNot Available
ChEBI ID15946
Food Biomarker OntologyNot Available
VMH IDF6P
MarkerDB IDMDB00000059
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in carbohydrate metabolic process
Specific function:
Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
Gene Name:
GNPDA1
Uniprot ID:
P46926
Molecular weight:
32668.29
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT2
Uniprot ID:
O94808
Molecular weight:
76929.885
Reactions
Glutamine + Fructose 6-phosphate → Glutamic acid + Glucosamine 6-phosphatedetails
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT1
Uniprot ID:
Q06210
Molecular weight:
78805.81
Reactions
Glutamine + Fructose 6-phosphate → Glutamic acid + Glucosamine 6-phosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKP
Uniprot ID:
Q01813
Molecular weight:
85595.405
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKM
Uniprot ID:
P08237
Molecular weight:
85181.925
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB3
Uniprot ID:
Q16875
Molecular weight:
57286.965
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
General function:
Involved in mannose-6-phosphate isomerase activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions.
Gene Name:
MPI
Uniprot ID:
P34949
Molecular weight:
46655.44
Reactions
Mannose 6-phosphate → Fructose 6-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB4
Uniprot ID:
Q16877
Molecular weight:
54039.34
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB1
Uniprot ID:
P16118
Molecular weight:
54680.86
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails

Only showing the first 10 proteins. There are 18 proteins in total.