Record Information
Version1.0
Creation date2011-09-21 00:13:17 UTC
Update date2018-05-29 01:52:48 UTC
Primary IDFDB022390
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Fructose 2,6-bisphosphate
DescriptionD-Fructose 2,6-bisphosphate is a regulatory molecule controlling the activity of the enzyme Phosphofructokinase-1 or PFK1 (in mammals). PFK1, in turn, is the key regulatory enzyme in the central metabolic pathway Glycolysis. D-Fructose 2,6-bisphosphate has the effect of increasing the activity of PFK1, thus increasing the rate at which the principle food molecule glucose is broken down. At the same time, this regulatory molecule also inhibits the opposing enzyme (FBPase1) in the reverse pathway (gluconeogenesis) so that the synthesis of glucose is not taking place in the same cell where glucose is being broken down (which would be wasteful) . [HMDB]
CAS Number79082-92-1
Structure
Thumb
Synonyms
SynonymSource
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-biphosphateHMDB
Fructose 2,6-diphosphateHMDB
Phosphofructokinase activation factorHMDB
Phosphofructokinase activatorHMDB
Fructose-2,6-diphosphateHMDB
2,6-Di-O-ONO-b-D-fructofuranoseGenerator
2,6-Di-O-ONO-beta-D-fructofuranoseChEBI
2,6-Di-O-ONO-β-D-fructofuranoseGenerator
b-D-Fructose 2,6-bisateHMDB
b-D-fructose 2,6-bisphosphatehmdb
beta-D-Fructose 2,6-bisateHMDB
beta-D-fructose 2,6-bisphosphatehmdb
D-Fructose 2,6-bisateChEBI
D-Fructose 2,6-bisic acidGenerator
D-Fructose 2,6-bisphosphatehmdb
D-Fructose 2,6-bisphosphic acidhmdb
Fru 2,6-P2, fructose 2,6-diateHMDB
Fru 2,6-P2, Fructose 2,6-diphosphatehmdb
Fructose 2,6-bisateHMDB
fructose 2,6-bisphosphatehmdb
Predicted Properties
PropertyValueSource
Water Solubility15.8 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H14O12P2
IUPAC name{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=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
Isomeric SMILESOC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
Classification
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
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9512000000-82418e0e398490357c5eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-2190010000-53cf738181713979e181JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3797000000-cb11e27ce8d0be902a39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9132000000-b908246df46f54e31180JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-9600000000-19262e5981934144e1aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7409000000-0240bd8771cde252759cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-8930f98e412f1b68e30bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fb204edc71835bcbaaadJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID94762
ChEMBL IDNot Available
KEGG Compound IDC00665
Pubchem Compound ID105021
Pubchem Substance IDNot Available
ChEBI ID28602
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01047
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35645
KNApSAcK IDNot Available
HET IDFDP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3PFKFB3Q16875
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4PFKFB4Q16877
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1PFKFB1P16118
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2PFKFB2O60825
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference