Fructose-6-phosphate

Identification

Generic Name
Fructose-6-phosphate
DrugBank Accession Number
DB04493
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 260.1358
Monoisotopic: 260.029718526
Chemical Formula
C6H13O9P
Synonyms
  • D-Fructose 6-phosphate
  • D-Fructose 6-phosphoric acid
  • keto-D-fructose 6-phosphate
  • Neuberg ester

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acyloin / Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Alpha-hydroxy ketone / Beta-hydroxy ketone / Carbonyl group / Hexose phosphate / Hydrocarbon derivative / Ketone
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-fructose 6-phosphate (CHEBI:15946)
Affected organisms
Not Available

Chemical Identifiers

UNII
2012QM764Y
CAS number
643-13-0
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

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
Human Metabolome Database
HMDB0000124
PubChem Compound
69507
PubChem Substance
46507447
ChemSpider
62713
ChEBI
15946
ZINC
ZINC000085994845
PDBe Ligand
F6R
Wikipedia
Fructose_6-phosphate
PDB Entries
1fqo / 1x9h / 2bkx / 2gc2 / 2put / 2v4m / 3opq / 3s1v / 3t2e / 3te9
show 17 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability20.78 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-MSsplash10-0k97-9840000000-4f9f16f21249d9870dfa
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0aor-0690000000-b640c7fba12f06d6bfa2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01oy-5390000000-74038b75062d5208c727
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9300000000-d1f6840b6c9514245b46
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9200000000-1fa98210932877f01eef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-9000000000-68e2a2413db514aab39e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-94914cb528dffe170fcb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-f06c76fd42524853c864
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.5046446
predicted
DarkChem Lite v0.1.0
[M-H]-159.8474446
predicted
DarkChem Lite v0.1.0
[M-H]-153.3365446
predicted
DarkChem Lite v0.1.0
[M-H]-148.27754
predicted
DeepCCS 1.0 (2019)
[M+H]+155.7320446
predicted
DarkChem Lite v0.1.0
[M+H]+159.0554446
predicted
DarkChem Lite v0.1.0
[M+H]+155.9705446
predicted
DarkChem Lite v0.1.0
[M+H]+150.67311
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.6668446
predicted
DarkChem Lite v0.1.0
[M+Na]+156.9197446
predicted
DarkChem Lite v0.1.0
[M+Na]+154.9295446
predicted
DarkChem Lite v0.1.0
[M+Na]+156.61427
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52