beta-D-fructofuranose 1,6-bisphosphate

Identification

Name
beta-D-fructofuranose 1,6-bisphosphate
Accession Number
DB04551  (EXPT01395)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1,6-di-O-phosphono-β-D-fructofuranose
  • beta-D-Fructose 1,6-bisphosphate
  • β-D-fructofuranose 1,6-bisphosphate
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 340.1157
Monoisotopic: 339.996048936
Chemical Formula
C6H14O12P2
InChI Key
RNBGYGVWRKECFJ-ARQDHWQXSA-N
InChI
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
IUPAC Name
{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPyruvate kinase PKLRNot AvailableHuman
UGlycerol kinaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hiroshi Nakajima, Masaaki Onda, Ryoichi Turutani, Hayato Ishihara, "Process for producing fructose-1,6-diphosphate." U.S. Patent US5094947, issued January, 1981.

US5094947
General References
Not Available
External Links
Human Metabolome Database
HMDB60444
KEGG Compound
C05378
PubChem Compound
10267
PubChem Substance
46506743
ChemSpider
9848
ChEBI
28013
ChEMBL
CHEMBL97893
HET
FBP
PDB Entries
1a3w / 1a5z / 1bo5 / 1fbh / 1lbz / 1ldn / 1lth / 1pfk / 1t5a / 1w8s
show 38 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m3·mol-1ChemAxon
Polarizability25.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9869
Blood Brain Barrier+0.861
Caco-2 permeable-0.7258
P-glycoprotein substrateNon-substrate0.6486
P-glycoprotein inhibitor INon-inhibitor0.7814
P-glycoprotein inhibitor IINon-inhibitor0.9866
Renal organic cation transporterNon-inhibitor0.9078
CYP450 2C9 substrateNon-substrate0.8227
CYP450 2D6 substrateNon-substrate0.8283
CYP450 3A4 substrateNon-substrate0.5902
CYP450 1A2 substrateNon-inhibitor0.885
CYP450 2C9 inhibitorNon-inhibitor0.887
CYP450 2D6 inhibitorNon-inhibitor0.9141
CYP450 2C19 inhibitorNon-inhibitor0.853
CYP450 3A4 inhibitorNon-inhibitor0.9808
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9835
Ames testNon AMES toxic0.8163
CarcinogenicityNon-carcinogens0.8938
BiodegradationReady biodegradable0.5232
Rat acute toxicity2.0919 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8747
hERG inhibition (predictor II)Non-inhibitor0.8611
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (7 TMS)GC-MSsplash10-014i-0497100000-d0c0dfadfe65ee3cc4e5
GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)GC-MSsplash10-014r-1779100000-ba60994aacef73cf8691
GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)GC-MSsplash10-014r-0779100000-b52ccd042ce4169961ed
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-6469000000-934f8ed1edcbd28bc667
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-006y-7295000000-a5ca0806e65ba8c99e88
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-9700000000-02fcc2f4b95b801c5949
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-8509000000-2992f67772e061c3ffe5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9ac5383c77bff5f6cb96
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9d902dae0eabfe2165da

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Hexose phosphates
Alternative Parents
Pentose phosphates / C-glycosyl compounds / Monosaccharide phosphates / Monoalkyl phosphates / Tetrahydrofurans / Secondary alcohols / Hemiacetals / 1,2-diols / Oxacyclic compounds / Organic oxides
show 1 more
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
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-fructofuranose 1,6-bisphosphate (CHEBI:28013)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyruvate kinase activity
Specific Function
Plays a key role in glycolysis.
Gene Name
PKLR
Uniprot ID
P30613
Uniprot Name
Pyruvate kinase PKLR
Molecular Weight
61829.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Key enzyme in the regulation of glycerol uptake and metabolism. Catalyzes the phosphorylation of glycerol to yield sn-glycerol 3-phosphate. It also catalyzes the phosphorylation of dihydroxyacetone...
Gene Name
glpK
Uniprot ID
P0A6F3
Uniprot Name
Glycerol kinase
Molecular Weight
56230.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [PubMed:11997326]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:43