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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:39:07 UTC
HMDB IDHMDB0001058
Secondary Accession Numbers
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
Data?1582752173
Synonyms
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number34693-15-7
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 KeyRNBGYGVWRKECFJ-ARQDHWQXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • 1,2-diol
  • Hemiacetal
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility94 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg150.330932474
[M-H]-Not Available157.509http://allccs.zhulab.cn/database/detail?ID=AllCCS00001809
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB04551
Phenol Explorer Compound IDNot Available
FooDB IDFDB022397
KNApSAcK IDNot Available
Chemspider ID9848
KEGG Compound IDC05378
BioCyc IDFRUCTOSE-16-DIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkFructose 1,6-bisphosphate
METLIN ID147
PubChem Compound10267
PDB IDBFP
ChEBI ID28013
Food Biomarker OntologyNot Available
VMH IDFDP
MarkerDB IDNot Available
Good Scents IDNot Available
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;2:18. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:1204623 ]
  7. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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
Adenosine triphosphate + Beta-D-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
Adenosine triphosphate + Beta-D-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
Adenosine triphosphate + Beta-D-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 + Phosphatedetails
Fructose 1,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
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 + Phosphatedetails
Fructose 1,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphate → Fructose 1,6-bisphosphatedetails
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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + 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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + 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

Only showing the first 10 proteins. There are 14 proteins in total.