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Human Metabolome Database Version 3.5

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Showing metabocard for Fructose 1,6-bisphosphate (HMDB01058)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-03-12 16:21:28 -0600
HMDB ID HMDB01058
Secondary Accession Numbers
  • HMDB03973
Metabolite Identification
Common Name Fructose 1,6-bisphosphate
Description Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. D-Fructose 1,6-biphosphate
  2. D-Fructose 1,6-bis(dihydrogen phosphate)
  3. D-Fructose 1,6-bisphosphate
  4. D-Fructose 1,6-diphosphate
  5. D-Fructose-1,6-bisphosphate
  6. D-Fructose-1,6-diphosphate
  7. Diphosphofructose
  8. Esafosfan
  9. Esafosfina
  10. FDP
  11. Fosfructose
  12. Fructose 1,6-bis
  13. Fructose 1,6-bisphosphate
  14. Fructose 1,6-diphosphate
  15. Harden-Young ester
Chemical Formula C6H14O12P2
Average Molecular Weight 340.1157
Monoisotopic Molecular Weight 339.996048936
IUPAC Name {[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name fructose 1,6-bisphosphate
CAS Registry Number 488-69-7
SMILES O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI Identifier InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
InChI Key RNBGYGVWRKECFJ-ZXXMMSQZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Monosaccharide Phosphates
Substituents
  • 1,2 Diol
  • Dialkyl Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Pentoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Inositol metabolism
  • Protein component
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 94 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 16.1 g/L ALOGPS
LogP -1.51 ALOGPS
LogP -3 ChemAxon
LogS -1.33 ALOGPS
pKa (strongest acidic) 0.89 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 203.44 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 58.11 ChemAxon
Polarizability 25.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location Not Available
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
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
3.8 +/- 0.7 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
1.2 +/- 0.4 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
7.60 (3.60-11.6) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022397
KNApSAcK ID Not Available
Chemspider ID 393165 Link_out
KEGG Compound ID C00354 Link_out
BioCyc ID FRUCTOSE-16-DIPHOSPHATE Link_out
BiGG ID 34717 Link_out
Wikipedia Link Fructose 1,6-diphosphate Link_out
NuGOwiki Link HMDB01058 Link_out
Metagene Link HMDB01058 Link_out
METLIN ID 147 Link_out
PubChem Compound 172313 Link_out
PDB ID AFP Link_out
ChEBI ID 16905 Link_out
References
Synthesis Reference Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-9, table of contents. Pubmed: 14693576 Link_out
  2. Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. Pubmed: 8412001 Link_out
  3. 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
  4. Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. Pubmed: 11916152 Link_out
  5. Ahn SM, Yoon HY, Lee BG, Park KC, Chung JH, Moon CH, Lee SH: Fructose-1,6-diphosphate attenuates prostaglandin E2 production and cyclo-oxygenase-2 expression in UVB-irradiated HaCaT keratinocytes. Br J Pharmacol. 2002 Oct;137(4):497-503. Pubmed: 12359631 Link_out
  6. Norne JE, Lilja H, Lindman B, Einarsson R, Zeppezauer M: Pt(CN)2-4 and Au(CN)-2: potential general probes for anion-binding sites of proteins. 35Cl and 81Br nuclear-magnetic-resonance studies. Eur J Biochem. 1975 Nov 15;59(2):463-73. Pubmed: 1204623 Link_out
Enzymes
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: 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: Fructose-bisphosphate aldolase A
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOA
Uniprot ID: P04075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase C
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOC
Uniprot ID: P09972 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase B
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOB
Uniprot ID: P05062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: Not Available
Uniprot ID: Q8NHT3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOC
Uniprot ID: A8MVZ9 Link_out
Protein Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: Not Available
Uniprot ID: A4UCT0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: Not Available
Uniprot ID: A4UCS9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOB
Uniprot ID: Q5T7D5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: Not Available
Uniprot ID: A8K430 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA