alpha-D-glucose 6-phosphate

Identification

Name
alpha-D-glucose 6-phosphate
Accession Number
DB02007  (EXPT01537)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 6-O-phosphono-α-D-glucopyranose
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 260.1358
Monoisotopic: 260.029718526
Chemical Formula
C6H13O9P
InChI Key
NBSCHQHZLSJFNQ-DVKNGEFBSA-N
InChI
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1
IUPAC Name
{[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHexokinase-1Not AvailableHuman
UPhosphomannomutase/phosphoglucomutaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UMaltose-6'-phosphate glucosidaseNot AvailableBacillus subtilis (strain 168)
UGlycogen phosphorylase, muscle formNot AvailableHuman
UAlpha,alpha-trehalose-phosphate synthase [UDP-forming]Not AvailableEscherichia coli (strain K12)
UGlutamine--fructose-6-phosphate aminotransferase [isomerizing]Not AvailableEscherichia coli (strain K12)
U6-phospho-beta-glucosidase BglTNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UGlucose-6-phosphate isomeraseNot AvailableHuman
UAldose reductaseNot 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

General References
Not Available
External Links
KEGG Compound
C00668
PubChem Compound
439284
PubChem Substance
46505235
ChemSpider
388417
ChEBI
17665
HET
G6P
PDB Entries
1bg3 / 1cza / 1gpy / 1gz5 / 1hkb / 1mor / 1p5g / 1qha / 1u0f / 1u8x
show 29 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 Solubility31.4 mg/mLALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9918
Blood Brain Barrier+0.8315
Caco-2 permeable-0.7235
P-glycoprotein substrateNon-substrate0.6687
P-glycoprotein inhibitor INon-inhibitor0.8225
P-glycoprotein inhibitor IINon-inhibitor0.9931
Renal organic cation transporterNon-inhibitor0.9062
CYP450 2C9 substrateNon-substrate0.8113
CYP450 2D6 substrateNon-substrate0.8365
CYP450 3A4 substrateNon-substrate0.574
CYP450 1A2 substrateNon-inhibitor0.9182
CYP450 2C9 inhibitorNon-inhibitor0.9049
CYP450 2D6 inhibitorNon-inhibitor0.9189
CYP450 2C19 inhibitorNon-inhibitor0.8947
CYP450 3A4 inhibitorNon-inhibitor0.9695
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9722
Ames testNon AMES toxic0.7495
CarcinogenicityNon-carcinogens0.9233
BiodegradationReady biodegradable0.5726
Rat acute toxicity2.1534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9149
hERG inhibition (predictor II)Non-inhibitor0.8981
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0490000000-1a5b3049c27a2a9b8996
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dm-4940000000-cbc695bef22278b36879
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uka-8900000000-320e52be29673422365e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-6290000000-e76ad7d6142e19f5a9c2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-e27be76de6d71ada7083
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9540d84c7e74555e7a01
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-9000000000-968c6c3b67e18b5f76ee
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9400000000-7915b6ed71501fad3fc4
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-e8b45476ee838b1a65f3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-a539479c0fdb3773b79c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-e7f6a8f6fd02eb7302a4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-3a7b06dc151f201c7fec

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 / Oxanes / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Hexose phosphate / Monosaccharide phosphate / Monoalkyl phosphate / Organic phosphoric acid derivative / Alkyl phosphate / Oxane / Phosphoric acid ester / Hemiacetal / Secondary alcohol / Oxacycle
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-glucopyranose 6-phosphate (CHEBI:17665)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Mannokinase activity
Specific Function
Not Available
Gene Name
HK1
Uniprot ID
P19367
Uniprot Name
Hexokinase-1
Molecular Weight
102485.1 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
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Phosphomannomutase activity
Specific Function
Highly reversible phosphoryltransferase. The phosphomannomutase activity produces a precursor for alginate polymerization, the alginate layer causes a mucoid phenotype and provides a protective bar...
Gene Name
algC
Uniprot ID
P26276
Uniprot Name
Phosphomannomutase/phosphoglucomutase
Molecular Weight
50295.09 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
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function
Hydrolyzes maltose-6'-phosphate and trehalose-6'-phosphate. Is involved in the catabolism of alpha-glycosides accumulated via a phosphoenolpyruvate-dependent maltose phosphotransferase system (PEP-...
Gene Name
glvA
Uniprot ID
P54716
Uniprot Name
Maltose-6'-phosphate glucosidase
Molecular Weight
50513.14 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
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Alpha,alpha-trehalose-phosphate synthase (udp-forming) activity
Specific Function
Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Es...
Gene Name
otsA
Uniprot ID
P31677
Uniprot Name
Alpha,alpha-trehalose-phosphate synthase [UDP-forming]
Molecular Weight
53610.655 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
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
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function
Hydrolyzes cellobiose 6'-phosphate into glucose 6-phosphate (Glc6P) and glucose.
Gene Name
bglT
Uniprot ID
Q9X108
Uniprot Name
6-phospho-beta-glucosidase BglT
Molecular Weight
47626.38 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:51