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Human Metabolome Database Version 3.5

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Showing metabocard for Glucose 6-phosphate (HMDB01401)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:28 -0700
HMDB ID HMDB01401
Secondary Accession Numbers
  • HMDB01549
  • HMDB06793
Metabolite Identification
Common Name Glucose 6-phosphate
Description Glucose 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number 56-73-5
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 Key NBSCHQHZLSJFNQ-GASJEMHNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Galactose metabolism
  • Component of Glutathione metabolism
  • Component of Starch and sucrose metabolism
Application Not Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 31.4 g/L ALOGPS
LogP -2.06 ALOGPS
LogP -3.1 ChemAxon
LogS -0.92 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.8 ChemAxon
Polarizability 20.56 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Kidney
  • Liver
  • Adrenal Gland
  • Adipose Tissue
Pathways
Name SMPDB Link KEGG Link
Gluconeogenesis SMP00128 map00010 Link_out
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Inositol Metabolism SMP00011 map00562 Link_out
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Glycolysis SMP00040 map00010 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Nucleotide Sugars Metabolism SMP00010 map00520 Link_out
Inositol Phosphate Metabolism SMP00462 map00562 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
4.52 +/- 8.7 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
29.1 +/- 6.8 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
38.0 (26.0-50.0) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021818
KNApSAcK ID Not Available
Chemspider ID 5743 Link_out
KEGG Compound ID C00092 Link_out
BioCyc ID GLC-6-P Link_out
BiGG ID 36977 Link_out
Wikipedia Link Glucose 6-phosphate Link_out
NuGOwiki Link HMDB01401 Link_out
Metagene Link HMDB01401 Link_out
METLIN ID 145 Link_out
PubChem Compound 5958 Link_out
PDB ID 1JXA Link_out
ChEBI ID 4170 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  3. Roden M: How free fatty acids inhibit glucose utilization in human skeletal muscle. News Physiol Sci. 2004 Jun;19:92-6. Pubmed: 15143200 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
  16. 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 Link_out
  17. 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 Link_out
  18. 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 Link_out
  19. 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 Link_out
  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 Link_out
Enzymes
Name: Glucokinase
Reactions:
  • ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate 1-dehydrogenase
Reactions:
  • D-glucose 6-phosphate + NADP+ = D-glucono-1,5-lactone 6-phosphate + NADPH + H+ [RN:R00835]
Gene Name: G6PD
Uniprot ID: P11413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ADP-dependent glucokinase
Reactions:
  • ADP + D-glucose = AMP + D-glucose 6-phosphate [RN:R05804]
Gene Name: ADPGK
Uniprot ID: Q9BRR6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, liver form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGL
Uniprot ID: P06737 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, muscle form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGM
Uniprot ID: P11217 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, brain form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGB
Uniprot ID: P11216 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphatase
Reactions:
  • D-glucose 6-phosphate + H2O = D-glucose + phosphate [RN:R00303]
Gene Name: G6PC
Uniprot ID: P35575 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate isomerase
Reactions:
  • D-glucose 6-phosphate = D-fructose 6-phosphate [RN:R00771]
Gene Name: GPI
Uniprot ID: P06744 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglucomutase-1
Reactions:
  • alpha-D-glucose 1-phosphate = D-glucose 6-phosphate [RN:R08639]
Gene Name: PGM1
Uniprot ID: P36871 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate translocase
Reactions:
    Gene Name: SLC37A4
    Uniprot ID: O43826 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glucokinase regulatory protein
    Reactions:
      Gene Name: GCKR
      Uniprot ID: Q14397 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glucose-6-phosphatase 3
      Reactions:
      • D-glucose 6-phosphate + H2O = D-glucose + phosphate [RN:R00303]
      Gene Name: G6PC3
      Uniprot ID: Q9BUM1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glucose-6-phosphatase 2
      Reactions:
      • D-glucose 6-phosphate + H2O = D-glucose + phosphate [RN:R00303]
      Gene Name: G6PC2
      Uniprot ID: Q9NQR9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Inositol-3-phosphate synthase 1
      Reactions:
      • D-glucose 6-phosphate = 1D-myo-inositol 3-phosphate [RN:R07324]
      Gene Name: ISYNA1
      Uniprot ID: Q9NPH2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA