Showing metabocard for D-Fructose 2,6-bisphosphate (BMDB0001047)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:21 UTC
Update Date2020-05-19 22:01:06 UTC
BMDB IDBMDB0001047
Secondary Accession Numbers
  • BMDB01047
Metabolite Identification
Common NameD-Fructose 2,6-bisphosphate
DescriptionD-D-d-fructose 2,6-bisphosphate, also known as d-fructose 2,6-bisphosphate, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-D-d-fructose 2,6-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-D-d-fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-D-d-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In cattle, D-d-fructose 2,6-bisphosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,6-Di-O-phosphono-beta-D-fructofuranoseChEBI
2,6-Di-O-phosphono-b-D-fructofuranoseGenerator
2,6-Di-O-phosphono-β-D-fructofuranoseGenerator
D-Fructose 2,6-bisphosphoric acidGenerator
b-D-Fructose 2,6-bisphosphateHMDB
beta-D-Fructose 2,6-bisphosphateHMDB
Fru 2,6-P2, fructose 2,6-diphosphateHMDB
Fructose 2,6-bisphosphateHMDB
Fructose 2,6-biphosphateMeSH, HMDB
Fructose 2,6-diphosphateMeSH, HMDB
Phosphofructokinase activation factorMeSH, HMDB
Phosphofructokinase activatorMeSH, HMDB
Fructose-2,6-diphosphateMeSH, HMDB
D-Fructose 2,6-diphosphateHMDB
beta-D-Fructose 2,6-diphosphateHMDB
β-D-Fructose 2,6-diphosphateHMDB
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional Namefructose-2,6-diphosphate
CAS Registry Number79082-92-1
SMILES
OC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
InChI KeyYXWOAJXNVLXPMU-ZXXMMSQZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.68ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001047
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022390
KNApSAcK IDC00007441
Chemspider ID94762
KEGG Compound IDC00665
BioCyc IDCPD-535
BiGG ID35645
Wikipedia LinkFructose_2,6-bisphosphate
METLIN ID5964
PubChem Compound105021
PDB IDNot Available
ChEBI ID28602
References
Synthesis ReferenceShulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB1
Uniprot ID:
P49872
Molecular weight:
54657.0
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphatedetails
Enzyme Details
2. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB3
Uniprot ID:
Q28901
Molecular weight:
53584.0
Enzyme Details
3. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2
General function:
Carbohydrate transport and metabolism
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB2
Uniprot ID:
P26285
Molecular weight:
60811.0
Enzyme Details
4. Fructose-2,6-bisphosphatase TIGAR
General function:
Carbohydrate transport and metabolism
Specific function:
Fructose-bisphosphatase hydrolyzing fructose-2,6-bisphosphate as well as fructose-1,6-bisphosphate (By similarity). Acts as a negative regulator of glycolysis by lowering intracellular levels of fructose-2,6-bisphosphate in a p53/TP53-dependent manner, resulting in the pentose phosphate pathway (PPP) activation and NADPH production. Contributes to the generation of reduced glutathione to cause a decrease in intracellular reactive oxygen species (ROS) content, correlating with its ability to protect cells from oxidative or metabolic stress-induced cell death. Plays a role in promoting protection against cell death during hypoxia by decreasing mitochondria ROS levels in a HK2-dependent manner through a mechanism that is independent of its fructose-bisphosphatase activity. In response to cardiac damage stress, mediates p53-induced inhibition of myocyte mitophagy through ROS levels reduction and the subsequent inactivation of BNIP3. Reduced mitophagy results in an enhanced apoptotic myocyte cell death, and exacerbates cardiac damage. Plays a role in adult intestinal regeneration; contributes to the growth, proliferation and survival of intestinal crypts following tissue ablation. Plays a neuroprotective role against ischemic brain damage by enhancing PPP flux and preserving mitochondria functions. Protects glioma cells from hypoxia- and ROS-induced cell death by inhibiting glycolysis and activating mitochondrial energy metabolism and oxygen consumption in a TKTL1-dependent and p53/TP53-independent manner. Plays a role in cancer cell survival by promoting DNA repair through activating PPP flux in a CDK5-ATM-dependent signaling pathway during hypoxia and/or genome stress-induced DNA damage responses. Involved in intestinal tumor progression.
Gene Name:
TIGAR
Uniprot ID:
Q1JQA7
Molecular weight:
29467.0