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Record Information
Version1.0
Creation Date2016-09-30 22:19:51 UTC
Update Date2020-05-21 16:28:40 UTC
BMDB IDBMDB0000124
Secondary Accession Numbers
  • BMDB00124
Metabolite Identification
Common NameFructose 6-phosphate
DescriptionFructose 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 possibly soluble (in water) and 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
Thumb
Synonyms
ValueSource
D-Fructose 6-phosphateChEBI
D-Fructose 6-phosphoric acidChEBI
Fructose-6-phosphateChEBI
Neuberg esterChEBI
Fructose-6-phosphoric acidGenerator
Fructose 6-phosphoric acidGenerator
D-Fructose 6-phosphorateHMDB
D-Fructose-6-pHMDB
D-Fructose-6-phosphateHMDB
FPCHMDB
Fru-6-pHMDB
Fructose-6-pHMDB
Fructose-6PHMDB
Fructose-6-phosphate, (alpha-D)-isomerHMDB
Fructose-6-phosphate, (beta-D)-isomerHMDB
Fructose-6-phosphate, disodium salt, (D)-isomerHMDB
Fructose-6-phosphate, (D)-isomerHMDB
Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomerHMDB
Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomerHMDB
Fructose-6-phosphate, barium (1:1) salt, (D)-isomerHMDB
Fructose-6-phosphate, barium salt, (D)-isomerHMDB
Fructose-6-phosphate, sodium salt, (D)-isomerHMDB
Fructose-6-phosphate, calcium salt, (D)-isomerHMDB
Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomerHMDB
Fructose-6-phosphate, sodium saltHMDB
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility911 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m³·mol⁻¹ChemAxon
Polarizability20.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-0gba-1943000000-9b9bb3f9964b519fa26bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1943000000-0be5d726668730e99be0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1954000000-9fa83268db2925e9478dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000b-0934000000-eb61ccae8d0b23564bc7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000b-0934000000-c2a49f4f2d11d3e60a9eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000j-0925000000-a6b6a121cb447c890019View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f7a-1934000000-b28e738e5093324060d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-3966000000-fee84a4ec7828d92e8b6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-1955000000-32da70382eccbcbbb574View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-1943000000-9b9bb3f9964b519fa26bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1943000000-0be5d726668730e99be0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1954000000-9fa83268db2925e9478dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-0934000000-eb61ccae8d0b23564bc7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-0934000000-c2a49f4f2d11d3e60a9eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-0925000000-a6b6a121cb447c890019View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7a-1934000000-b28e738e5093324060d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3966000000-fee84a4ec7828d92e8b6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1955000000-32da70382eccbcbbb574View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-1933000000-1c8febd80da1382bec31View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k97-9840000000-4f9f16f21249d9870dfaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00o9-7934540000-e23e661c1babf5e063a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0229-5090000000-281699f4bce06db0b1b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006x-9730000000-b72576e6bb1ae73e6881View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kbf-9740000000-130bb715a91e870b5480View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-9710000000-5d6429381cefb6a2bdc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9100000000-51c3f5ca7ef3f190f1dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-054k-9000000000-75c50b162633f723546dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-07895e6c6f3e4a816391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3590000000-3fc4dac2f46082421870View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c04-9610000000-77e7a6ced5ab4dda6f86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-e4500e644878a4632447View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ar9-9720000000-7ca18e5a32ef069ff21aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-00032f32c05509571a9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5e859d2084880df68725View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Intestine
  • Liver
  • Mammary Gland
  • Milk
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000124
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
Q2TBL6
Molecular weight:
37685.0
General function:
Carbohydrate transport and metabolism
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
Q58DR3
Molecular weight:
23712.0
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB1
Uniprot ID:
P49872
Molecular weight:
54657.0
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations and probably participates in glycogen synthesis from carbohydrate precursors, such as lactate.
Gene Name:
FBP2
Uniprot ID:
Q2KJJ9
Molecular weight:
36767.0
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB3
Uniprot ID:
Q28901
Molecular weight:
53584.0
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB2
Uniprot ID:
P26285
Molecular weight:
60811.0
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations, acting as a rate-limiting enzyme in gluconeogenesis. Plays a role in regulating glucose sensing and insulin secretion of pancreatic beta-cells. Appears to modulate glycerol gluconeogenesis in liver. Important regulator of appetite and adiposity; increased expression of the protein in liver after nutrient excess increases circulating satiety hormones and reduces appetite-stimulating neuropeptides and thus seems to provide a feedback mechanism to limit weight gain.
Gene Name:
FBP1
Uniprot ID:
Q3SZB7
Molecular weight:
36728.0
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis (By similarity). Negatively regulates the phagocyte oxidative burst in response to bacterial infection by controlling cellular NADPH biosynthesis and NADPH oxidase-derived reactive oxygen species. Upon macrophage activation, drives the metabolic switch toward glycolysis, thus preventing glucose turnover that produces NADPH via pentose phosphate pathway (By similarity).
Gene Name:
PFKL
Uniprot ID:
A1A4J1
Molecular weight:
85292.0
Reactions
Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADPdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
Gene Name:
PFKM
Uniprot ID:
Q0IIG5
Molecular weight:
85294.0
General function:
Energy production and conversion
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
Q6B855
Molecular weight:
67906.0
Reactions
D-Erythrose 4-phosphate + Xylulose 5-phosphate → Fructose 6-phosphate + D-Glyceraldehyde 3-phosphatedetails
General function:
Cell wall/membrane/envelope biogenesis
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 (By similarity).
Gene Name:
GFPT2
Uniprot ID:
Q08DQ2
Molecular weight:
77081.0
Reactions
Fructose 6-phosphate + L-Glutamine → Glucosamine 6-phosphate + L-Glutamic aciddetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
D-Fructose + Adenosine triphosphate → Fructose 6-phosphate + ADPdetails
General function:
Carbohydrate transport and metabolism
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:
Q3SZI0
Molecular weight:
46369.0
Reactions
Mannose 6-phosphate → Fructose 6-phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Fructose-bisphosphatase hydrolyzing fructose-2,6-bisphosphate as well as fructose-1,6-bisphosphate (By similarity). Acts as a negative regulator of glycolysis by lowering intracellular levels of fructose-2,6-bisphosphate in a p53/TP53-dependent manner, resulting in the pentose phosphate pathway (PPP) activation and NADPH production. Contributes to the generation of reduced glutathione to cause a decrease in intracellular reactive oxygen species (ROS) content, correlating with its ability to protect cells from oxidative or metabolic stress-induced cell death. Plays a role in promoting protection against cell death during hypoxia by decreasing mitochondria ROS levels in a HK2-dependent manner through a mechanism that is independent of its fructose-bisphosphatase activity. In response to cardiac damage stress, mediates p53-induced inhibition of myocyte mitophagy through ROS levels reduction and the subsequent inactivation of BNIP3. Reduced mitophagy results in an enhanced apoptotic myocyte cell death, and exacerbates cardiac damage. Plays a role in adult intestinal regeneration; contributes to the growth, proliferation and survival of intestinal crypts following tissue ablation. Plays a neuroprotective role against ischemic brain damage by enhancing PPP flux and preserving mitochondria functions. Protects glioma cells from hypoxia- and ROS-induced cell death by inhibiting glycolysis and activating mitochondrial energy metabolism and oxygen consumption in a TKTL1-dependent and p53/TP53-independent manner. Plays a role in cancer cell survival by promoting DNA repair through activating PPP flux in a CDK5-ATM-dependent signaling pathway during hypoxia and/or genome stress-induced DNA damage responses. Involved in intestinal tumor progression.
Gene Name:
TIGAR
Uniprot ID:
Q1JQA7
Molecular weight:
29467.0
General function:
Carbohydrate transport and metabolism
Specific function:
In the cytoplasm, catalyzes the conversion of glucose-6-phosphate to fructose-6-phosphate, the second step in glycolysis, and the reverse reaction during gluconeogenesis (By similarity). Besides it's role as a glycolytic enzyme, also acts as a secreted cytokine: acts as an angiogenic factor (AMF) that stimulates endothelial cell motility. Acts as a neurotrophic factor, neuroleukin, for spinal and sensory neurons. It is secreted by lectin-stimulated T-cells and induces immunoglobulin secretion (By similarity).
Gene Name:
GPI
Uniprot ID:
Q3ZBD7
Molecular weight:
62855.0
Reactions
Fructose 6-phosphate → Glucose 6-phosphatedetails
Beta-D-Glucose 6-phosphate → Fructose 6-phosphatedetails
General function:
Not Available
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:
A4FV08
Molecular weight:
32580.0
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails