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Human Metabolome Database Version 3.5

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Showing metabocard for Beta-D-Fructose 6-phosphate (HMDB03971)

Record Information
Version 3.5
Creation Date 2006-08-13 02:16:58 -0600
Update Date 2013-02-08 17:12:53 -0700
HMDB ID HMDB03971
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-D-Fructose 6-phosphate
Description Beta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase (liver) and Transaldolase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. beta-D-Fructose 6-phosphate
Chemical Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number Not Available
SMILES OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1
InChI Key BGWGXPAPYGQALX-ARQDHWQXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • D-tagatose 6-phosphate(ChEBI)
  • Monosaccharide Phosphates
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Pentoses
Ontology
Status Expected and Not 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 Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 33.4 g/L ALOGPS
LogP -2.11 ALOGPS
LogP -2.9 ChemAxon
LogS -0.89 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 47.23 ChemAxon
Polarizability 20.91 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023276
KNApSAcK ID Not Available
Chemspider ID 389526 Link_out
KEGG Compound ID C05345 Link_out
BioCyc ID FRUCTOSE-6P Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03971 Link_out
Metagene Link HMDB03971 Link_out
METLIN ID Not Available
PubChem Compound 440641 Link_out
PDB ID F6P Link_out
ChEBI ID 16084 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
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. 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
  3. 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
  4. 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: Glucokinase
Reactions:
  • ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase type C
Reactions:
  • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
Gene Name: PFKP
Uniprot ID: Q01813 Link_out
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 Link_out
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 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3
Reactions:
  • beta-D-fructose 2,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00763]
Gene Name: PFKFB3
Uniprot ID: Q16875 Link_out
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 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 4
Reactions:
  • beta-D-fructose 2,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00763]
Gene Name: PFKFB4
Uniprot ID: Q16877 Link_out
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 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase-like protein 1
Reactions:
  • sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate [RN:R01641]
Gene Name: TKTL1
Uniprot ID: P51854 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-1,6-bisphosphatase isozyme 2
Reactions:
  • D-fructose 1,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00762]
Gene Name: FBP2
Uniprot ID: O00757 Link_out
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 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 2
Reactions:
  • beta-D-fructose 2,6-bisphosphate + H2O = D-fructose 6-phosphate + phosphate [RN:R00763]
Gene Name: PFKFB2
Uniprot ID: O60825 Link_out
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 Link_out
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 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase-like protein 2
Reactions:
  • sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate [RN:R01641]
Gene Name: TKTL2
Uniprot ID: Q9H0I9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA