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Showing Compound D-Fructose 1,6-bisphosphate (FDB022397)

Record Information
Version1.0
Creation date2011-09-21 00:13:23 UTC
Update date2020-09-17 15:38:47 UTC
Primary IDFDB022397
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Fructose 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. Within humans, fructose 1,6-bisphosphate participates in a number of enzymatic reactions. In particular, fructose 1,6-bisphosphate can be converted into fructose 6-phosphate through the action of the enzyme fructose-1,6-bisphosphatase 1. In addition, fructose 1,6-bisphosphate can be converted into dihydroxyacetone phosphate and D-glyceraldehyde 3-phosphate; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. In humans, fructose 1,6-bisphosphate is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Outside of the human body, Fructose 1,6-bisphosphate has been detected, but not quantified in, several different foods, such as rices, peach (var.), other soy products, celery leaves, and white lupines. This could make fructose 1,6-bisphosphate a potential biomarker for the consumption of these foods. A D-fructofuranose 1,6-bisphosphate with a beta-configuration at the anomeric position.
CAS Number488-69-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1,6-Di-O-ONO-a-D-fructofuranoseGenerator
1,6-Di-O-ONO-alpha-D-fructofuranoseChEBI
1,6-Di-O-ONO-α-D-fructofuranoseGenerator
a FRUCTOSE 1,6-diateGenerator
a FRUCTOSE 1,6-diic acidGenerator
ALPHA FRUCTOSE 1,6-diATEChEBI
alpha FRUCTOSE 1,6-diic acidGenerator
D-Fructose 1,6-biateHMDB
D-Fructose 1,6-bis(dihydrogen ate)HMDB
D-Fructose 1,6-bisateHMDB
D-Fructose 1,6-diateHMDB
D-Fructose-1,6-bisateHMDB
D-fructose-1,6-bisphosphatehmdb
D-Fructose-1,6-diateHMDB
D-fructose-1,6-diphosphatehmdb
DiofructoseHMDB
Esafosfanhmdb
Esafosfinahmdb
FDPhmdb
Fructose 1,6-bisHMDB
Fructose 1,6-bisateHMDB
Fructose 1,6-diateHMDB
Harden-Young esterhmdb
α fructose 1,6-diateGenerator
α fructose 1,6-diic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H14O12P2
IUPAC name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=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
Isomeric SMILESO[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSD-Fructose 1,6-bisphosphate, 7 TMS, GC-MS Spectrumsplash10-014i-0497100000-d0c0dfadfe65ee3cc4e5Spectrum
GC-MSD-Fructose 1,6-bisphosphate, 1 MEOX; 7 TMS, GC-MS Spectrumsplash10-014r-1779100000-ba60994aacef73cf8691Spectrum
GC-MSD-Fructose 1,6-bisphosphate, 1 MEOX; 7 TMS, GC-MS Spectrumsplash10-014r-0779100000-b52ccd042ce4169961edSpectrum
Predicted GC-MSD-Fructose 1,6-bisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01xt-9532000000-c3c4929a4987e34c0dc0Spectrum
Predicted GC-MSD-Fructose 1,6-bisphosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fs-9412510000-0a0a9e96cc6bea61e3c7Spectrum
Predicted GC-MSD-Fructose 1,6-bisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0006-0190000000-95a4b5217606c0b9d1fb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0002-0900000000-74a1700e0fae0f6aa64e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-0009000000-631b4fa683b46f4c89cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-1009000000-9df66c58adba653741e02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000j-7129000000-f1414a0a896a7c132d2d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-0002-9111000000-0fc51e8f6b123f0a59822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0002-9100000000-762070874ad885772dc42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-0002-9100000000-d705002b3a24c5b5ac0f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-002b-9000000000-caf9814ab914b20935612020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-004j-9000000000-3b04f1a6a67ed239b0012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-388ef99a8af7f88e64472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-004i-9000000000-bc85bd9d38f2c4bf3c582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0006-0190000000-ba22a78fbbfc1a90ace32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0a4i-0900000000-b559d4679fc0eaa79be72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0002-9530000000-8e5076b641ebc42fb2ef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0fdk-9870000000-6332e12e884d56a6c22b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-6469000000-934f8ed1edcbd28bc6672015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-7295000000-a5ca0806e65ba8c99e882015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9700000000-02fcc2f4b95b801c59492015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-8509000000-2992f67772e061c3ffe52015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-9ac5383c77bff5f6cb962015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9d902dae0eabfe2165da2015-09-15View Spectrum
NMRNot Available
ChemSpider ID393165
ChEMBL IDCHEMBL1089962
KEGG Compound IDC00354
Pubchem Compound ID445557
Pubchem Substance IDNot Available
ChEBI ID16905
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01058
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34717
KNApSAcK IDNot Available
HET IDAFP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFructose 1,6-diphosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Fructose-bisphosphate aldolase AALDOAP04075
Fructose-bisphosphate aldolase CALDOCP09972
Fructose-bisphosphate aldolase BALDOBP05062
Fructose-1,6-bisphosphatase isozyme 2FBP2O00757
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
GluconeogenesisSMP00128 map00010
GlycolysisSMP00040 map00010
Pentose Phosphate PathwaySMP00031 map00030
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference