Record Information
Version1.0
Creation date2011-04-11 17:01:45 UTC
Update date2019-11-26 03:20:54 UTC
Primary IDFDB021818
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucose 6-phosphate
DescriptionGlucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Glucose 6 phosphate is 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). Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to Fructose-6-phosphate and then phosphorylated to Fructose-1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose-6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase a during times of high stress or low blood glucose levels. -- Wikipedia [HMDB]
CAS Number56-73-5
Structure
Thumb
Synonyms
SynonymSource
6-O-ONO-D-GlucopyranoseChEBI
a-D-Glucose 6- ateHMDB
alpha-D-Glucose 6- ateHMDB
alpha-D-Glucose 6-ateHMDB
alpha-D-Hexose 6-ateHMDB
D-Glucose 6-ateChEBI
D-Glucose 6-ic acidGenerator
D-Glucose-6-dihydrogen ateHMDB
D-Hexose 6-ateHMDB
D(+)-Glucopyranose 6-ateHMDB
Glc6PChEBI
Glucose 6-ateHMDB
Glucose-6-ateHMDB
Robison esterChEBI
Predicted Properties
PropertyValueSource
Water Solubility31.4 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H39O27P3
IUPAC name[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]phosphonic acid; [(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]phosphonic acid; [2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)ethoxy]phosphonic acid
InChI IdentifierInChI=1S/3C6H13O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5;7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8;7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h2*2-10H,1H2,(H2,11,12,13);1,3-6,8-11H,2H2,(H2,12,13,14)
InChI KeyNVBMVWKTLWOTGR-UHFFFAOYSA-N
Isomeric SMILESOC(COP(O)(O)=O)C(O)C(O)C(O)C=O.OC(COP(O)(O)=O)C1OC(O)C(O)C1O.OC1OC(COP(O)(O)=O)C(O)C(O)C1O
Average Molecular Weight780.4073
Monoisotopic Molecular Weight780.089155578
Classification
DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID5743
ChEMBL IDNot Available
KEGG Compound IDC00092
Pubchem Compound ID5958
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01401
CRC / DFC (Dictionary of Food Compounds) IDBVF14-F:BVF15-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36977
KNApSAcK IDNot Available
HET ID1JXA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glucose-6-phosphate 1-dehydrogenaseG6PDP11413
Glycogen phosphorylase, liver formPYGLP06737
Glycogen phosphorylase, muscle formPYGMP11217
Glycogen phosphorylase, brain formPYGBP11216
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
Glucokinase regulatory proteinGCKRQ14397
Glucose-6-phosphataseG6PCP35575
Glucose-6-phosphatase 2G6PC2Q9NQR9
Glucose-6-phosphate isomeraseGPIP06744
Glucose-6-phosphatase 3G6PC3Q9BUM1
Glucose-6-phosphate translocaseSLC37A4O43826
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
GluconeogenesisSMP00128 map00010
GlycolysisSMP00040 map00010
Inositol MetabolismSMP00011 map00562
Inositol Phosphate MetabolismSMP00462 map00562
Nucleotide Sugars MetabolismSMP00010 map00520
Pentose Phosphate PathwaySMP00031 map00030
Starch and Sucrose MetabolismSMP00058 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference