Showing metabocard for Fructose 1,6-bisphosphate (BMDB0001058)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:30 UTC
Update Date2020-05-19 22:01:06 UTC
BMDB IDBMDB0001058
Secondary Accession Numbers
  • BMDB01058
Metabolite Identification
Common NameFructose 1,6-bisphosphate
DescriptionFructose 1,6-bisphosphate, also known as fosfructose or SR-FDP, 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. Fructose 1,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 1,6-bisphosphate exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,6-Di-O-phosphono-beta-D-fructofuranoseChEBI
BETA FRUCTOSE 1,6-diphosphATEChEBI
beta-D-Fructose 1,6-bisphosphateChEBI
FosfructoseChEBI
1,6-Di-O-phosphono-b-D-fructofuranoseGenerator
1,6-Di-O-phosphono-β-D-fructofuranoseGenerator
b FRUCTOSE 1,6-diphosphateGenerator
b FRUCTOSE 1,6-diphosphoric acidGenerator
beta FRUCTOSE 1,6-diphosphoric acidGenerator
Β fructose 1,6-diphosphateGenerator
Β fructose 1,6-diphosphoric acidGenerator
b-D-Fructose 1,6-bisphosphateGenerator
b-D-Fructose 1,6-bisphosphoric acidGenerator
beta-D-Fructose 1,6-bisphosphoric acidGenerator
Β-D-fructose 1,6-bisphosphateGenerator
Β-D-fructose 1,6-bisphosphoric acidGenerator
Fructose 1,6-bisphosphoric acidGenerator
Fructose-1,6-diphosphateHMDB
Fructose-1,6-diphosphate, calcium saltHMDB
Fructose-1,6-diphosphate, disodium saltHMDB
Fructose-1,6-diphosphate, trisodium saltHMDB
Fructose-1,6-diphosphate, 2-(18)O-labeledHMDB
Fructose-1,6-diphosphate, calcium (1:2) saltHMDB
Fructose-1,6-diphosphate, monosodium saltHMDB
Strontium fructose 1,6-diphosphateHMDB
SR-FDPHMDB
Fructose 1,6-diphosphateHMDB
Fructose-1,6-diphosphate, (L)-isomerHMDB
Fructose-1,6-diphosphate, (alpha-D)-isomerHMDB
Fructose-1,6-diphosphate, barium (1:2) saltHMDB
Fructose-1,6-diphosphate, sodium salt, monohydrateHMDB
Fructose-1,6-diphosphate, tetrasodium saltHMDB
Strontium fructose-1,6-diphosphateHMDB
Fructose-1,6-diphosphate magnesium saltHMDB
Fructose-1,6-diphosphate, (beta-D)-isomerHMDB
Fructose-1,6-diphosphate, tetrapotassium saltHMDB
D-Fructose 1,6-biphosphateHMDB
D-Fructose 1,6-bisphosphateHMDB
D-Fructose 1,6-diphosphateHMDB
DiphosphofructoseHMDB
Fructose 1,6-bis(dihydrogen phosphate)HMDB
beta-D-Fructofuranose 1,6-bisphosphateHMDB
beta-D-Fructofuranose 1,6-diphosphateHMDB
beta-D-Fructose 1,6-diphosphateHMDB
Β-D-fructofuranose 1,6-bisphosphateHMDB
Β-D-fructofuranose 1,6-diphosphateHMDB
Β-D-fructose 1,6-diphosphateHMDB
Fructose 1,6-bisphosphateMeSH
b-D-Fructofuranose 1,6-bisphosphateGenerator
b-D-Fructofuranose 1,6-bisphosphoric acidGenerator
beta-D-Fructofuranose 1,6-bisphosphoric acidGenerator
Β-D-fructofuranose 1,6-bisphosphoric acidGenerator
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 NumberNot Available
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
StatusDetected 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)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001058
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
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)Not Available
General References
  1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Enzymes

Enzyme Details
1. Fructose-1,6-bisphosphatase isozyme 2
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations and probably participates in glycogen synthesis from carbohydrate precursors, such as lactate.
Gene Name:
FBP2
Uniprot ID:
Q2KJJ9
Molecular weight:
36767.0
Enzyme Details
2. Fructose-1,6-bisphosphatase 1
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations, acting as a rate-limiting enzyme in gluconeogenesis. Plays a role in regulating glucose sensing and insulin secretion of pancreatic beta-cells. Appears to modulate glycerol gluconeogenesis in liver. Important regulator of appetite and adiposity; increased expression of the protein in liver after nutrient excess increases circulating satiety hormones and reduces appetite-stimulating neuropeptides and thus seems to provide a feedback mechanism to limit weight gain.
Gene Name:
FBP1
Uniprot ID:
Q3SZB7
Molecular weight:
36728.0
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphatedetails
Enzyme Details
3. ATP-dependent 6-phosphofructokinase, liver type
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis (By similarity). Negatively regulates the phagocyte oxidative burst in response to bacterial infection by controlling cellular NADPH biosynthesis and NADPH oxidase-derived reactive oxygen species. Upon macrophage activation, drives the metabolic switch toward glycolysis, thus preventing glucose turnover that produces NADPH via pentose phosphate pathway (By similarity).
Gene Name:
PFKL
Uniprot ID:
A1A4J1
Molecular weight:
85292.0
Reactions
Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADPdetails
Enzyme Details
4. ATP-dependent 6-phosphofructokinase, muscle type
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
Gene Name:
PFKM
Uniprot ID:
Q0IIG5
Molecular weight:
85294.0
Enzyme Details
5. Fructose-bisphosphate aldolase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOA
Uniprot ID:
A6QLL8
Molecular weight:
39436.0
Enzyme Details
6. Fructose-bisphosphate aldolase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
Q3ZBY4
Molecular weight:
39382.0
Enzyme Details
7. Fructose-bisphosphate aldolase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
A5PK73
Molecular weight:
39527.0
Enzyme Details
8. Fructose-bisphosphate aldolase B
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
Q3T0S5
Molecular weight:
39543.0