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Human Metabolome Database Version 3.5

Showing metabocard for Fructose 6-phosphate (HMDB00124)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (10)

• Blood
• Urine

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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	D-Fructose 6-phosphate D-Fructose 6-phosphorate D-Fructose 6-phosphoric acid D-Fructose-6-P D-Fructose-6-phosphate FPC Fru-6-P Fructose 6-phosphate Fructose-6-P Fructose-6-phosphate Fructose-6P 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 Gluconeogenesis SMP00128 map00010 Fructose and Mannose Degradation SMP00064 map00051 Pentose Phosphate Pathway SMP00031 map00030 Amino Sugar Metabolism SMP00045 map00520
Normal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 9.9 +/- 2.3 uM Newborn (0-30 days old) Both Normal Not Available Blood Detected and Quantified 10.2 +/- 1.8 uM Adult (>18 years old) Both Normal Not Available Cellular Cytoplasm Detected and Quantified 16.0 (13.0-19.0) uM Adult (>18 years old) Both Normal Not Available Cellular Cytoplasm Detected and Quantified 49.6 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank 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
KEGG Compound ID	C00085
BioCyc ID	FRUCTOSE-6P
BiGG ID	33795
Wikipedia Link	Fructose 6-phosphate
NuGOwiki Link	HMDB00124
Metagene Link	HMDB00124
METLIN ID	5159
PubChem Compound	69507
PDB ID	F6R
ChEBI ID	15946
References
Synthesis Reference	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
General References	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 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 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 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 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 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 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 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 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

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Enzymes
Name: Glucosamine-6-phosphate isomerase 1 Reactions: D-glucosamine 6-phosphate + H2O = D-fructose 6-phosphate + NH3 [RN:R00765] Gene Name: GNPDA1 Uniprot ID: P46926 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 1 Reactions: L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate [RN:R00768] Gene Name: GFPT1 Uniprot ID: Q06210 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 6-phosphofructokinase, liver type Reactions: ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756] Gene Name: PFKL Uniprot ID: P17858 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 6-phosphofructokinase, muscle type Reactions: ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756] Gene Name: PFKM Uniprot ID: P08237 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Mannose-6-phosphate isomerase Reactions: D-mannose 6-phosphate = D-fructose 6-phosphate [RN:R00772] Gene Name: MPI Uniprot ID: P34949 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 1 Reactions: beta-D-fructose 2,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00763] Gene Name: PFKFB1 Uniprot ID: P16118 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Transaldolase Reactions: sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate [RN:R08575] Gene Name: TALDO1 Uniprot ID: P37837 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Fructose-1,6-bisphosphatase 1 Reactions: D-fructose 1,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00762] Gene Name: FBP1 Uniprot ID: P09467 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Transketolase Reactions: sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate [RN:R01641] Gene Name: TKT Uniprot ID: P29401 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glucose-6-phosphate isomerase Reactions: D-glucose 6-phosphate = D-fructose 6-phosphate [RN:R00771] Gene Name: GPI Uniprot ID: P06744 Protein Sequence: FASTA Gene Sequence: FASTA

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