Human Metabolome Database Version 3.5

Showing metabocard for Fructose 6-phosphate (HMDB00124)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:55 -0700
HMDB ID HMDB00124
Secondary Accession Numbers None
Metabolite Identification
Common Name Fructose 6-phosphate
Description Fructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. D-Fructose 6-phosphate
  2. D-Fructose 6-phosphorate
  3. D-Fructose 6-phosphoric acid
  4. D-Fructose-6-P
  5. D-Fructose-6-phosphate
  6. FPC
  7. Fru-6-P
  8. Fructose 6-phosphate
  9. Fructose-6-P
  10. Fructose-6-phosphate
  11. Fructose-6P
  12. Neuberg ester
Chemical Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxyphosphonic acid
CAS Registry Number 643-13-0
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 Key GSXOAOHZAIYLCY-HSUXUTPPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • ketohexose monophosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Acyloin
  • Alpha Ketoaldehyde
  • Beta Ketoaldehyde
  • Ketone
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Glutamate metabolism
  • Component of Starch and sucrose metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 911 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 23.2 g/L ALOGPS
LogP -1.86 ALOGPS
LogP -3.4 ChemAxon
LogS -1.05 ALOGPS
pKa (strongest acidic) 1.49 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 164.75 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 48.43 ChemAxon
Polarizability 20.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Intestine
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
9.9 +/- 2.3 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
10.2 +/- 1.8 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cellular Cytoplasm Detected and Quantified
16.0 (13.0-19.0) uM Adult (>18 years old) Both Normal
Cellular Cytoplasm Detected and Quantified
49.6 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021896
KNApSAcK ID Not Available
Chemspider ID 62713 Link_out
KEGG Compound ID C00085 Link_out
BioCyc ID FRUCTOSE-6P Link_out
BiGG ID 33795 Link_out
Wikipedia Link Fructose 6-phosphate Link_out
NuGOwiki Link HMDB00124 Link_out
Metagene Link HMDB00124 Link_out
METLIN ID 5159 Link_out
PubChem Compound 69507 Link_out
PDB ID F6R Link_out
ChEBI ID 15946 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. Markuszewski MJ, Szczykowska M, Siluk D, Kaliszan R: Human red blood cells targeted metabolome analysis of glycolysis cycle metabolites by capillary electrophoresis using an indirect photometric detection method. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):636-42. Pubmed: 15925468 Link_out
  4. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454 Link_out
  5. Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. Pubmed: 16055050 Link_out
  6. Karlander S, Roovete A, Vranic M, Efendic S: Glucose and fructose 6-phosphate cycle in humans. Am J Physiol. 1986 Nov;251(5 Pt 1):E530-6. Pubmed: 3777162 Link_out
  7. Gapparov MM, Virovets OA: [Nonenzymatic glycosylation of serum albumin and thymic DNA by food monosugars and their natural metabolites that form in the body] Vopr Pitan. 1990 Jan-Feb;(1):36-40. Pubmed: 2346009 Link_out
  8. Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95. Pubmed: 9451038 Link_out
  9. 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 Link_out
  10. 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 Link_out

Enzymes
Name: Glucosamine-6-phosphate isomerase 1
Reactions:
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammonia details
Gene Name: GNPDA1
Uniprot ID: P46926 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
Reactions:
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
Gene Name: GFPT2
Uniprot ID: O94808 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1
Reactions:
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
Gene Name: GFPT1
Uniprot ID: Q06210 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase type C
Reactions:
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphate details
Gene Name: PFKP
Uniprot ID: Q01813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase, liver type
Reactions:
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphate details
Gene Name: PFKL
Uniprot ID: P17858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase, muscle type
Reactions:
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphate details
Gene Name: PFKM
Uniprot ID: P08237 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3
Reactions:
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphate details
Gene Name: PFKFB3
Uniprot ID: Q16875 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mannose-6-phosphate isomerase
Reactions:
Mannose 6-phosphate unknown Fructose 6-phosphate details
Gene Name: MPI
Uniprot ID: P34949 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4
Reactions:
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphate details
Gene Name: PFKFB4
Uniprot ID: Q16877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
Reactions:
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphate details
Gene Name: PFKFB1
Uniprot ID: P16118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-1,6-bisphosphatase isozyme 2
Reactions:
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Gene Name: FBP2
Uniprot ID: O00757 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transaldolase
Reactions:
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Fructose 6-phosphate details
Gene Name: TALDO1
Uniprot ID: P37837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-1,6-bisphosphatase 1
Reactions:
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Gene Name: FBP1
Uniprot ID: P09467 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2
Reactions:
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphate details
Gene Name: PFKFB2
Uniprot ID: O60825 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase
Reactions: Not Available
Gene Name: TKT
Uniprot ID: P29401 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate isomerase
Reactions:
Glucose 6-phosphate unknown Fructose 6-phosphate details
Gene Name: GPI
Uniprot ID: P06744 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosamine-6-phosphate isomerase 2
Reactions:
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammonia details
Gene Name: GNPDA2
Uniprot ID: Q8TDQ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-2,6-bisphosphatase TIGAR
Reactions:
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric acid details
Gene Name: TIGAR
Uniprot ID: Q9NQ88 Link_out
Protein Sequence: FASTA