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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:28 UTC
HMDB IDHMDB01401
Secondary Accession Numbers
  • HMDB01549
  • HMDB06793
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
  1. a-D-Glucose 6- phosphate
  2. alpha-D-Glucose 6- phosphate
  3. alpha-D-Glucose 6-phosphate
  4. alpha-D-Hexose 6-phosphate
  5. D(+)-Glucopyranose 6-phosphate
  6. D-Glucose 6-phosphate
  7. D-Glucose-6-dihydrogen phosphate
  8. D-Hexose 6-phosphate
  9. Glucose 6-phosphate
  10. Glucose-6-phosphate
  11. Robison ester
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number56-73-5
SMILES
OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
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
InChI KeyNBSCHQHZLSJFNQ-GASJEMHNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-glucopyranose 6-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Galactose metabolism
  • Component of Glutathione metabolism
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility31.4 g/LALOGPS
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 Area156.91ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8ChemAxon
Polarizability20.56ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Fibroblasts
  • Kidney
  • Liver
  • Muscle
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Inositol MetabolismSMP00011map00562
Inositol Phosphate MetabolismSMP00462map00562
Nucleotide Sugars MetabolismSMP00010map00520
Pentose Phosphate PathwaySMP00031map00030
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.52 +/- 8.7 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified29.1 +/- 6.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified38.0 (26.0-50.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021818
KNApSAcK IDNot Available
Chemspider ID5743
KEGG Compound IDC00092
BioCyc IDGLC-6-P
BiGG ID36977
Wikipedia LinkGlucose 6-phosphate
NuGOwiki LinkHMDB01401
Metagene LinkHMDB01401
METLIN ID145
PubChem Compound5958
PDB ID1JXA
ChEBI ID4170
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  2. Price TB, Laurent D, Petersen KF: 13C/31P NMR studies on the role of glucose transport/phosphorylation in human glycogen supercompensation. Int J Sports Med. 2003 May;24(4):238-44. Pubmed: 12784164
  3. Boden G, Jadali F, White J, Liang Y, Mozzoli M, Chen X, Coleman E, Smith C: Effects of fat on insulin-stimulated carbohydrate metabolism in normal men. J Clin Invest. 1991 Sep;88(3):960-6. Pubmed: 1885781
  4. Lehto M, Xiang K, Stoffel M, Espinosa R 3rd, Groop LC, Le Beau MM, Bell GI: Human hexokinase II: localization of the polymorphic gene to chromosome 2. Diabetologia. 1993 Dec;36(12):1299-302. Pubmed: 8307259
  5. Brehm A, Krssak M, Schmid AI, Nowotny P, Waldhausl W, Roden M: Increased lipid availability impairs insulin-stimulated ATP synthesis in human skeletal muscle. Diabetes. 2006 Jan;55(1):136-40. Pubmed: 16380486
  6. Roden M: How free fatty acids inhibit glucose utilization in human skeletal muscle. News Physiol Sci. 2004 Jun;19:92-6. Pubmed: 15143200
  7. Chang PY, Jensen J, Printz RL, Granner DK, Ivy JL, Moller DE: Overexpression of hexokinase II in transgenic mice. Evidence that increased phosphorylation augments muscle glucose uptake. J Biol Chem. 1996 Jun 21;271(25):14834-9. Pubmed: 8662926
  8. Schalin-Jantti C, Harkonen M, Groop LC: Impaired activation of glycogen synthase in people at increased risk for developing NIDDM. Diabetes. 1992 May;41(5):598-604. Pubmed: 1568529
  9. Vaag A, Damsbo P, Hother-Nielsen O, Beck-Nielsen H: Hyperglycaemia compensates for the defects in insulin-mediated glucose metabolism and in the activation of glycogen synthase in the skeletal muscle of patients with type 2 (non-insulin-dependent) diabetes mellitus. Diabetologia. 1992 Jan;35(1):80-8. Pubmed: 1541385
  10. Fortpied J, Maliekal P, Vertommen D, Van Schaftingen E: Magnesium-dependent phosphatase-1 is a protein-fructosamine-6-phosphatase potentially involved in glycation repair. J Biol Chem. 2006 Jul 7;281(27):18378-85. Epub 2006 May 1. Pubmed: 16670083
  11. Cline GW, Petersen KF, Krssak M, Shen J, Hundal RS, Trajanoski Z, Inzucchi S, Dresner A, Rothman DL, Shulman GI: Impaired glucose transport as a cause of decreased insulin-stimulated muscle glycogen synthesis in type 2 diabetes. N Engl J Med. 1999 Jul 22;341(4):240-6. Pubmed: 10413736
  12. Foster JD, Pederson BA, Nordlie RC: Glucose-6-phosphatase structure, regulation, and function: an update. Proc Soc Exp Biol Med. 1997 Sep;215(4):314-32. Pubmed: 9270716
  13. Turvey EA, Heigenhauser GJ, Parolin M, Peters SJ: Elevated n-3 fatty acids in a high-fat diet attenuate the increase in PDH kinase activity but not PDH activity in human skeletal muscle. J Appl Physiol. 2005 Jan;98(1):350-5. Pubmed: 15591305
  14. Benkoel L, Chamlian A, Barrat E, Laffargue P: The use of ferricyanide for the electron microscopic demonstration of dehydrogenases in human steroidogenic cells. J Histochem Cytochem. 1976 Nov;24(11):1194-203. Pubmed: 1002973
  15. Villar-Palasi C, Guinovart JJ: The role of glucose 6-phosphate in the control of glycogen synthase. FASEB J. 1997 Jun;11(7):544-58. Pubmed: 9212078
  16. Vestergaard H, Bjorbaek C, Hansen T, Larsen FS, Granner DK, Pedersen O: Impaired activity and gene expression of hexokinase II in muscle from non-insulin-dependent diabetes mellitus patients. J Clin Invest. 1995 Dec;96(6):2639-45. Pubmed: 8675629
  17. Roussel R, Carlier PG, Wary C, Velho G, Bloch G: Evidence for 100% 13C NMR visibility of glucose in human skeletal muscle. Magn Reson Med. 1997 Jun;37(6):821-4. Pubmed: 9178231
  18. Cigolini M, Bonora E, Querena M, Moghetti P, Cacciatori V, Zancanaro C, Benati D, Muggeo M: Differences in glucose metabolic enzyme activities in human adipose tissue from abdominal and gluteal regions. Metabolism. 1988 Sep;37(9):820-3. Pubmed: 3419322
  19. Petersen KF, Hendler R, Price T, Perseghin G, Rothman DL, Held N, Amatruda JM, Shulman GI: 13C/31P NMR studies on the mechanism of insulin resistance in obesity. Diabetes. 1998 Mar;47(3):381-6. Pubmed: 9519743
  20. Boden G, Chen X, Ruiz J, White JV, Rossetti L: Mechanisms of fatty acid-induced inhibition of glucose uptake. J Clin Invest. 1994 Jun;93(6):2438-46. Pubmed: 8200979

Enzymes

General function:
Involved in ATP binding
Specific function:
Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
Gene Name:
GCK
Uniprot ID:
P35557
Molecular weight:
52191.07
Reactions
Adenosine triphosphate + D-Glucose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
Reactions
Adenosine triphosphate + D-Galactose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + D-Glucose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
Reactions
Adenosine triphosphate + D-Galactose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + D-Glucose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK1
Uniprot ID:
P19367
Molecular weight:
102485.1
Reactions
Adenosine triphosphate + D-Galactose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + D-Glucose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular weight:
62467.88
Reactions
Glucose 6-phosphate + NADP → 6-phospho-D-glucono-1,5-lactone + NADPHdetails
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
Gene Name:
H6PD
Uniprot ID:
O95479
Molecular weight:
88891.99
Reactions
Glucose 6-phosphate + NAD(P)(+) → 6-Phosphonoglucono-D-lactone + NAD(P)Hdetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the phosphorylation of D-glucose to D-glucose 6-phosphate using ADP as the phosphate donor. GDP and CDP can replace ADP, but with reduced efficiency (By similarity).
Gene Name:
ADPGK
Uniprot ID:
Q9BRR6
Molecular weight:
53960.185
Reactions
ADP + D-Glucose → Adenosine monophosphate + Glucose 6-phosphatedetails
Alpha-D-Glucose + ADP → Glucose 6-phosphate + Adenosine monophosphatedetails
General function:
Involved in phosphorylase activity
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 phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
General function:
Involved in phosphorylase activity
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 phosphorylases share catalytic and structural properties.
Gene Name:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355
General function:
Involved in phosphorylase activity
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 phosphorylases share catalytic and structural properties.
Gene Name:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes glucose-6-phosphate to glucose in the endoplasmic reticulum. Forms with the glucose-6-phosphate transporter (SLC37A4/G6PT) the complex responsible for glucose production through glycogenolysis and gluconeogenesis. Hence, it is the key enzyme in homeostatic regulation of blood glucose levels.
Gene Name:
G6PC
Uniprot ID:
P35575
Molecular weight:
40483.21
Reactions
Glucose 6-phosphate + Water → D-Glucose + Phosphoric aciddetails
Glucose 6-phosphate + Water → Alpha-D-Glucose + Phosphoric aciddetails
General function:
Involved in glucose-6-phosphate isomerase activity
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 neurotrophic factor (Neuroleukin) for spinal and sensory neurons.
Gene Name:
GPI
Uniprot ID:
P06744
Molecular weight:
63146.745
Reactions
Glucose 6-phosphate → Fructose 6-phosphatedetails
Glucose 6-phosphate → Beta-D-Glucose 6-phosphatedetails
Glucose 6-phosphate → Beta-D-Fructose 6-phosphatedetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:
PGM1
Uniprot ID:
P36871
Molecular weight:
63789.985
Reactions
Glucose 1-phosphate → Glucose 6-phosphatedetails
Glucose 1-phosphate → Glucose 6-phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Transports glucose-6-phosphate from the cytoplasm to the lumen of the endoplasmic reticulum. Forms with glucose-6- phosphatase the complex responsible for glucose production through glycogenolysis and gluconeogenesis. Hence, it plays a central role in homeostatic regulation of blood glucose levels
Gene Name:
SLC37A4
Uniprot ID:
O43826
Molecular weight:
46359.6
General function:
Involved in enzyme inhibitor activity
Specific function:
Inhibits glucokinase by forming an inactive complex with this enzyme
Gene Name:
GCKR
Uniprot ID:
Q14397
Molecular weight:
68700.7
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of the nucleoside breakdown products ribose-1-phosphate and deoxyribose-1-phosphate to the corresponding 5-phosphopentoses. May also catalyze the interconversion of glucose-1-phosphate and glucose-6-phosphate. Has low glucose 1,6-bisphosphate synthase activity.
Gene Name:
PGM2
Uniprot ID:
Q96G03
Molecular weight:
68282.765
Reactions
Glucose 1-phosphate → Glucose 6-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes glucose-6-phosphate to glucose in the endoplasmic reticulum. May form with the glucose-6-phosphate transporter (SLC37A4/G6PT) a ubiquitously expressed complex responsible for glucose production through glycogenolysis and gluconeogenesis. Probably required for normal neutrophil function.
Gene Name:
G6PC3
Uniprot ID:
Q9BUM1
Molecular weight:
38734.115
Reactions
Glucose 6-phosphate + Water → D-Glucose + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
May hydrolyze glucose-6-phosphate to glucose in the endoplasmic reticulum. May be responsible for glucose production through glycogenolysis and gluconeogenesis (By similarity).
Gene Name:
G6PC2
Uniprot ID:
Q9NQR9
Molecular weight:
17756.465
Reactions
Glucose 6-phosphate + Water → D-Glucose + Phosphoric aciddetails
Glucose 6-phosphate + Water → Alpha-D-Glucose + Phosphoric aciddetails
General function:
Involved in inositol-3-phosphate synthase activity
Specific function:
Key enzyme in myo-inositol biosynthesis pathway that catalyzes the conversion of glucose 6-phosphate to 1-myo-inositol 1-phosphate in a NAD-dependent manner. Rate-limiting enzyme in the synthesis of all inositol-containing compounds.
Gene Name:
ISYNA1
Uniprot ID:
Q9NPH2
Molecular weight:
55135.445
Reactions
Glucose 6-phosphate → Myo-inositol 1-phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Molecular weight:
102513.88
Reactions
Adenosine triphosphate + D-Galactose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + D-Glucose → ADP + Glucose 6-phosphatedetails
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails