Fructose-6-Phosphate

Identification

Name
Fructose-6-Phosphate
Accession Number
DB04493  (EXPT01383)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
2012QM764Y
CAS number
Not Available
Weight
Average: 260.1358
Monoisotopic: 260.029718526
Chemical Formula
C6H13O9P
InChI Key
GSXOAOHZAIYLCY-HSUXUTPPSA-N
InChI
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
IUPAC Name
{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
SMILES
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFructose-1,6-bisphosphatase 1Not AvailableHuman
U6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1Not AvailableHuman
U6-phosphofructokinaseNot AvailableGeobacillus stearothermophilus
U6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4Not AvailableHuman
UGlucose-6-phosphate isomeraseNot AvailableHuman
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

Kazunori Nishi, Yukiko Hikichi, Yasushi Shintani, "Glutamine: fructose-6-phosphate amidotransferase, its production and use." U.S. Patent US5876713, issued October, 1993.

US5876713
General References
Not Available
External Links
Human Metabolome Database
HMDB0000124
PubChem Compound
69507
PubChem Substance
46507447
ChemSpider
62713
ChEBI
15946
HET
F6R
PDB Entries
1fqo / 1x9h / 2bkx / 2gc2 / 2put / 2v4m / 3opq / 3s1v / 3t2e / 3te9
show 10 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 Solubility23.2 mg/mLALOGPS
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m3·mol-1ChemAxon
Polarizability20.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9611
Blood Brain Barrier+0.8427
Caco-2 permeable-0.719
P-glycoprotein substrateNon-substrate0.6769
P-glycoprotein inhibitor INon-inhibitor0.7754
P-glycoprotein inhibitor IINon-inhibitor0.9852
Renal organic cation transporterNon-inhibitor0.9036
CYP450 2C9 substrateNon-substrate0.8058
CYP450 2D6 substrateNon-substrate0.8213
CYP450 3A4 substrateNon-substrate0.598
CYP450 1A2 substrateNon-inhibitor0.8775
CYP450 2C9 inhibitorNon-inhibitor0.8872
CYP450 2D6 inhibitorNon-inhibitor0.9132
CYP450 2C19 inhibitorNon-inhibitor0.8535
CYP450 3A4 inhibitorNon-inhibitor0.9779
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9722
Ames testNon AMES toxic0.8428
CarcinogenicityNon-carcinogens0.8882
BiodegradationReady biodegradable0.5929
Rat acute toxicity2.0213 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8777
hERG inhibition (predictor II)Non-inhibitor0.8459
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)GC-MSsplash10-0gba-1943000000-9b9bb3f9964b519fa26b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)GC-MSsplash10-014j-1943000000-0be5d726668730e99be0
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)GC-MSsplash10-014j-1954000000-9fa83268db2925e9478d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000b-0934000000-eb61ccae8d0b23564bc7
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000b-0934000000-c2a49f4f2d11d3e60a9e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000j-0925000000-a6b6a121cb447c890019
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f7a-1934000000-b28e738e5093324060d9
GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)GC-MSsplash10-014i-3966000000-fee84a4ec7828d92e8b6
GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)GC-MSsplash10-014i-1955000000-32da70382eccbcbbb574
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gba-1943000000-9b9bb3f9964b519fa26b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014j-1943000000-0be5d726668730e99be0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014j-1954000000-9fa83268db2925e9478d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000b-0934000000-eb61ccae8d0b23564bc7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000b-0934000000-c2a49f4f2d11d3e60a9e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000j-0925000000-a6b6a121cb447c890019
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f7a-1934000000-b28e738e5093324060d9
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-3966000000-fee84a4ec7828d92e8b6
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1955000000-32da70382eccbcbbb574
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gba-1933000000-1c8febd80da1382bec31
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0229-5090000000-281699f4bce06db0b1b0
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-006x-9730000000-b72576e6bb1ae73e6881
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0kbf-9740000000-130bb715a91e870b5480
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0aor-0690000000-b640c7fba12f06d6bfa2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00kb-9710000000-5d6429381cefb6a2bdc7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0002-9100000000-51c3f5ca7ef3f190f1df
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-054k-9000000000-75c50b162633f723546d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-004i-9000000000-07895e6c6f3e4a816391
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0aor-0690000000-b640c7fba12f06d6bfa2
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
Monosaccharide phosphates / Monoalkyl phosphates / Beta-hydroxy ketones / Acyloins / Alpha-hydroxy ketones / Secondary alcohols / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Hexose phosphate / Monosaccharide phosphate / Monoalkyl phosphate / Acyloin / Beta-hydroxy ketone / Organic phosphoric acid derivative / Phosphoric acid ester / Alkyl phosphate / Alpha-hydroxy ketone / Ketone
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-fructose 6-phosphate (CHEBI:15946)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Monosaccharide binding
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 gl...
Gene Name
FBP1
Uniprot ID
P09467
Uniprot Name
Fructose-1,6-bisphosphatase 1
Molecular Weight
36842.145 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name
PFKFB1
Uniprot ID
P16118
Uniprot Name
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
Molecular Weight
54680.86 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Metal ion binding
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
pfkA
Uniprot ID
P00512
Uniprot Name
ATP-dependent 6-phosphofructokinase
Molecular Weight
34118.62 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
Human
Pharmacological action
Unknown
General Function
Fructose-2,6-bisphosphate 2-phosphatase activity
Specific Function
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name
PFKFB4
Uniprot ID
Q16877
Uniprot Name
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4
Molecular Weight
54039.34 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Besides it's role as a glycolytic enzyme, mammalian GPI can function as a tumor-secreted cytokine and an angiogenic factor (AMF) that stimulates endothelial cell motility. GPI is also a neurotrophi...
Gene Name
GPI
Uniprot ID
P06744
Uniprot Name
Glucose-6-phosphate isomerase
Molecular Weight
63146.745 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:51