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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:46 UTC
HMDB IDHMDB01058
Secondary Accession Numbers
  • HMDB03973
Metabolite Identification
Common NameFructose 1,6-bisphosphate
DescriptionFructose 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
Synonyms
ValueSource
1,6-Di-O-phosphono-alpha-D-fructofuranoseChEBI
ALPHA FRUCTOSE 1,6-diphosphATEChEBI
1,6-Di-O-phosphono-a-D-fructofuranoseGenerator
1,6-Di-O-phosphono-α-D-fructofuranoseGenerator
D-Fructose 1,6-biphosphateHMDB
D-Fructose 1,6-bis(dihydrogen phosphate)HMDB
D-Fructose 1,6-bisphosphateHMDB
D-Fructose 1,6-diphosphateHMDB
D-Fructose-1,6-bisphosphateHMDB
D-Fructose-1,6-diphosphateHMDB
DiphosphofructoseHMDB
EsafosfanHMDB
EsafosfinaHMDB
FDPHMDB
FosfructoseHMDB
Fructose 1,6-bisHMDB
Fructose 1,6-diphosphateHMDB
Harden-young esterHMDB
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional Namefructose 1,6-bisphosphate
CAS Registry Number488-69-7
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 KeyInChIKey=RNBGYGVWRKECFJ-ZXXMMSQZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Inositol metabolism
  • Protein component
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility94 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 mg/mLALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m3·mol-1ChemAxon
Polarizability25.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fanconi-bickel syndromeSMP00572Not Available
Fructose and Mannose DegradationSMP00064map00051
Fructose intolerance, hereditarySMP00725Not Available
Fructose-1,6-diphosphatase deficiencySMP00562Not Available
FructosuriaSMP00561Not Available
GluconeogenesisSMP00128map00010
Glucose-6-phosphate dehydrogenase deficiencySMP00518Not Available
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseSMP00374Not Available
Glycogenosis, Type IA. Von gierke diseaseSMP00581Not Available
Glycogenosis, Type IBSMP00573Not Available
Glycogenosis, Type ICSMP00574Not Available
Glycogenosis, Type VII. Tarui diseaseSMP00531Not Available
GlycolysisSMP00040map00010
Pentose Phosphate PathwaySMP00031map00030
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)SMP00560Not Available
Ribose-5-phosphate isomerase deficiencySMP00519Not Available
Transaldolase deficiencySMP00520Not Available
Triosephosphate isomeraseSMP00563Not Available
Warburg EffectSMP00654Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.8 +/- 0.7 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.2 +/- 0.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified7.60 (3.60-11.6) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022397
KNApSAcK IDNot Available
Chemspider ID393165
KEGG Compound IDC00354
BioCyc IDFRUCTOSE-16-DIPHOSPHATE
BiGG ID34717
Wikipedia LinkFructose 1,6-diphosphate
NuGOwiki LinkHMDB01058
Metagene LinkHMDB01058
METLIN ID147
PubChem Compound172313
PDB IDAFP
ChEBI ID16905
References
Synthesis ReferenceYan, 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. 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. [15882454 ]
  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. [8412001 ]
  3. 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. [14693576 ]
  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. [11916152 ]
  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. [12359631 ]
  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. [1204623 ]

Enzymes

General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKP
Uniprot ID:
Q01813
Molecular weight:
85595.405
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKM
Uniprot ID:
P08237
Molecular weight:
85181.925
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
Not Available
Gene Name:
FBP2
Uniprot ID:
O00757
Molecular weight:
36742.84
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Phosphoric aciddetails
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
Not Available
Gene Name:
FBP1
Uniprot ID:
P09467
Molecular weight:
36842.145
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Phosphoric aciddetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:
ALDOA
Uniprot ID:
P04075
Molecular weight:
39419.675
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
P09972
Molecular weight:
39455.505
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
P05062
Molecular weight:
39472.715
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
Not Available
Uniprot ID:
Q8NHT3
Molecular weight:
34750.6
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
ALDOC
Uniprot ID:
A8MVZ9
Molecular weight:
36294.9
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
Not Available
Uniprot ID:
A4UCT0
Molecular weight:
13349.3
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
Not Available
Uniprot ID:
A4UCS9
Molecular weight:
15551.7
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
ALDOB
Uniprot ID:
Q5T7D5
Molecular weight:
24128.5
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
Not Available
Uniprot ID:
A8K430
Molecular weight:
39471.8