Identification

Name
Glucose-6-Phosphate
Accession Number
DB03581  (EXPT01538)
Type
Small Molecule
Groups
Experimental
Description

An ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose-6-phosphate. (Stedman, 26th ed)

Structure
Thumb
Synonyms
Not Available
Categories
UNII
375AW34SQA
CAS number
56-73-5
Weight
Average: 260.1358
Monoisotopic: 260.029718526
Chemical Formula
C6H13O9P
InChI Key
VFRROHXSMXFLSN-KCDKBNATSA-N
InChI
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,8-11H,2H2,(H2,12,13,14)/t3-,4+,5+,6-/m0/s1
IUPAC Name
{[(2R,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl]oxy}phosphonic acid
SMILES
O[C@H](COP(O)(O)=O)[C@H](O)[C@H](O)[C@@H](O)C=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamine--fructose-6-phosphate aminotransferase [isomerizing]Not AvailableEscherichia coli (strain K12)
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

Hitoshi Sagai, Kimiko Hattori, Mamoru Takahashi, "Gene and process of making glucose-6-phosphate dehydrogenase." U.S. Patent US5137821, issued August, 1988.

US5137821
General References
Not Available
External Links
KEGG Compound
C00092
PubChem Compound
3034794
PubChem Substance
46508559
ChemSpider
2299195
BindingDB
197174
ChEBI
17733
HET
G6Q
Wikipedia
Glucose_6-phosphate

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 Solubility21.7 mg/mLALOGPS
logP-1.8ALOGPS
logP-3.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.22 m3·mol-1ChemAxon
Polarizability20.66 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9398
Blood Brain Barrier+0.8712
Caco-2 permeable-0.7722
P-glycoprotein substrateNon-substrate0.6644
P-glycoprotein inhibitor INon-inhibitor0.8863
P-glycoprotein inhibitor IINon-inhibitor0.9504
Renal organic cation transporterNon-inhibitor0.9504
CYP450 2C9 substrateNon-substrate0.83
CYP450 2D6 substrateNon-substrate0.8441
CYP450 3A4 substrateNon-substrate0.6316
CYP450 1A2 substrateNon-inhibitor0.9099
CYP450 2C9 inhibitorNon-inhibitor0.9024
CYP450 2D6 inhibitorNon-inhibitor0.9125
CYP450 2C19 inhibitorNon-inhibitor0.8943
CYP450 3A4 inhibitorNon-inhibitor0.9397
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9802
Ames testNon AMES toxic0.8295
CarcinogenicityNon-carcinogens0.726
BiodegradationReady biodegradable0.7151
Rat acute toxicity2.0202 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9696
hERG inhibition (predictor II)Non-inhibitor0.8889
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 (1 MEOX; 6 TMS)GC-MSsplash10-0f7a-2968100000-32d06d0209e91012d185
GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)GC-MSsplash10-0frj-2966100000-74964dbe57af64bc0edb
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Monosaccharide phosphates
Alternative Parents
Monoalkyl phosphates / Beta-hydroxy aldehydes / Alpha-hydroxyaldehydes / Secondary alcohols / Polyols / Organic oxides / Hydrocarbon derivatives
Substituents
Monosaccharide phosphate / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Beta-hydroxy aldehyde / Alpha-hydroxyaldehyde / Secondary alcohol / Polyol / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-galactose 6-phosphate (CHEBI:17733)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Glutamine-fructose-6-phosphate transaminase (isomerizing) activity
Specific Function
Catalyzes the first step in hexosamine metabolism, converting fructose-6P into glucosamine-6P using glutamine as a nitrogen source.
Gene Name
glmS
Uniprot ID
P17169
Uniprot Name
Glutamine--fructose-6-phosphate aminotransferase [isomerizing]
Molecular Weight
66893.7 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
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. 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]

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 02, 2018 05:37