Record Information
Version2.0
Creation Date2012-07-30 14:55:22 -0600
Update Date2015-09-13 12:56:15 -0600
Secondary Accession Numbers
  • ECMDB21341
Identification
Name:Glycogen
Description:Glycogen is a highly branched glucose polymer. It is formed of small chains of 8 to 12 glucose molecules linked together with (1->4) bonds. These small chains are in turn linked together with (1->6) bonds. A single molecule of glycogen can be made of up to 120,000 molecules of glucose. It is stored in the form of granules in the cytosol. (EcoCyc) Glycogen only has one reducing end and a large number of non-reducing ends with a free hydroxyl group at carbon 4. The glycogen granules contain both glycogen and the enzymes of glycogen synthesis (glycogenesis) and degradation (glycogenolysis). The enzymes are nested between the outer branches of the glycogen molecules and act on the non-reducing ends. Therefore, the many non-reducing end-branches of glycogen facilitate its rapid synthesis and breakdown. (HMDB)
Structure
Thumb
Synonyms:
  • Animal starch
  • Glycogen
  • Liver starch
  • Lyoglycogen
  • Phytoglycogen
Chemical Formula:C24H42O21
Weight:Average: 666.5777
Monoisotopic: 666.221858406
InChI Key:BYSGBSNPRWKUQH-UJDJLXLFSA-N
InChI:InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1
CAS number:9005-79-2
IUPAC Name:(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Name:glycogen
SMILES:OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:270-280 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility343 g/LALOGPS
logP-2.7ALOGPS
logP-8.2ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)11.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area347.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.16 m³·mol⁻¹ChemAxon
Polarizability61.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Secondary metabolites: Trehalose Biosynthesis and MetabolismPW000968 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0401739000-7d2f2aaa7732e23ef9feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0505921000-56fc10eb2d6cb63bc487View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0043-1906412000-81ae228fd873321b008cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gbj-0400339000-de452d5dddd55d2855ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004s-3901435000-bc5da17144e98986d7b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4839321000-4dfca4172b8470e37b09View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Chryssanthopoulos C, Williams C, Nowitz A, Bogdanis G: Skeletal muscle glycogen concentration and metabolic responses following a high glycaemic carbohydrate breakfast. J Sports Sci. 2004 Nov-Dec;22(11-12):1065-71. Pubmed: 15801500
  • Crosson SM, Khan A, Printen J, Pessin JE, Saltiel AR: PTG gene deletion causes impaired glycogen synthesis and developmental insulin resistance. J Clin Invest. 2003 May;111(9):1423-32. Pubmed: 12727934
  • Devries MC, Hamadeh MJ, Graham TE, Tarnopolsky MA: 17beta-estradiol supplementation decreases glucose rate of appearance and disappearance with no effect on glycogen utilization during moderate intensity exercise in men. J Clin Endocrinol Metab. 2005 Nov;90(11):6218-25. Epub 2005 Aug 23. Pubmed: 16118338
  • Dube SN, Nayak BB, Das PK: Effect of foot-electroshock stress on cholinergic activity, tissue glycogen and blood sugar in albino rats. Indian J Physiol Pharmacol. 1978 Jan-Mar;22(1):24-32. Pubmed: 567191
  • Hudson ER, Pan DA, James J, Lucocq JM, Hawley SA, Green KA, Baba O, Terashima T, Hardie DG: A novel domain in AMP-activated protein kinase causes glycogen storage bodies similar to those seen in hereditary cardiac arrhythmias. Curr Biol. 2003 May 13;13(10):861-6. Pubmed: 12747836
  • Jentjens R, Jeukendrup A: Determinants of post-exercise glycogen synthesis during short-term recovery. Sports Med. 2003;33(2):117-44. Pubmed: 12617691
  • Kohler G, Boutellier U: Glycogen reduction in non-exercising muscle depends on blood lactate concentration. Eur J Appl Physiol. 2004 Aug;92(4-5):548-54. Pubmed: 15170570
  • Koopman R, Manders RJ, Jonkers RA, Hul GB, Kuipers H, van Loon LJ: Intramyocellular lipid and glycogen content are reduced following resistance exercise in untrained healthy males. Eur J Appl Physiol. 2006 Mar;96(5):525-34. Epub 2005 Dec 21. Pubmed: 16369816
  • Koppersmith DL, Powers JM, Hennigar GR: Angiomatoid neuroblastoma with cytoplasmic glycogen: a case report and histogenetic considerations. Cancer. 1980 Feb;45(3):553-60. Pubmed: 7353205
  • McVie-Wylie AJ, Ding EY, Lawson T, Serra D, Migone FK, Pressley D, Mizutani M, Kikuchi T, Chen YT, Amalfitano A: Multiple muscles in the AMD quail can be "cross-corrected" of pathologic glycogen accumulation after intravenous injection of an [E1-, polymerase-] adenovirus vector encoding human acid-alpha-glucosidase. J Gene Med. 2003 May;5(5):399-406. Pubmed: 12731088
  • Ouwens DM, van der Zon GC, Maassen JA: Modulation of insulin-stimulated glycogen synthesis by Src Homology Phosphatase 2. Mol Cell Endocrinol. 2001 Apr 25;175(1-2):131-40. Pubmed: 11325523
  • 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
  • Schaart G, Hesselink RP, Keizer HA, van Kranenburg G, Drost MR, Hesselink MK: A modified PAS stain combined with immunofluorescence for quantitative analyses of glycogen in muscle sections. Histochem Cell Biol. 2004 Aug;122(2):161-9. Epub 2004 Aug 3. Pubmed: 15322861
  • Steinberg GR, Watt MJ, McGee SL, Chan S, Hargreaves M, Febbraio MA, Stapleton D, Kemp BE: Reduced glycogen availability is associated with increased AMPKalpha2 activity, nuclear AMPKalpha2 protein abundance, and GLUT4 mRNA expression in contracting human skeletal muscle. Appl Physiol Nutr Metab. 2006 Jun;31(3):302-12. Pubmed: 16770359
  • Tanis AA, Rietveld T, Wattimena JL, van den Berg JW, Swart GR: The 13CO2 breath test for liver glycogen oxidation after 3-day labeling of the liver with a naturally 13C-enriched diet. Nutrition. 2003 May;19(5):432-7. Pubmed: 12714096
  • Tomihira M, Kawasaki E, Nakajima H, Imamura Y, Sato Y, Sata M, Kage M, Sugie H, Nunoi K: Intermittent and recurrent hepatomegaly due to glycogen storage in a patient with type 1 diabetes: genetic analysis of the liver glycogen phosphorylase gene (PYGL). Diabetes Res Clin Pract. 2004 Aug;65(2):175-82. Pubmed: 15223230
  • van Loon LJ, Murphy R, Oosterlaar AM, Cameron-Smith D, Hargreaves M, Wagenmakers AJ, Snow R: Creatine supplementation increases glycogen storage but not GLUT-4 expression in human skeletal muscle. Clin Sci (Lond). 2004 Jan;106(1):99-106. Pubmed: 14507259
  • Wee SL, Williams C, Tsintzas K, Boobis L: Ingestion of a high-glycemic index meal increases muscle glycogen storage at rest but augments its utilization during subsequent exercise. J Appl Physiol. 2005 Aug;99(2):707-14. Epub 2005 Apr 14. Pubmed: 15831796
  • Zderic TW, Schenk S, Davidson CJ, Byerley LO, Coyle EF: Manipulation of dietary carbohydrate and muscle glycogen affects glucose uptake during exercise when fat oxidation is impaired by beta-adrenergic blockade. Am J Physiol Endocrinol Metab. 2004 Dec;287(6):E1195-201. Epub 2004 Aug 17. Pubmed: 15315908
  • Zehnder M, Muelli M, Buchli R, Kuehne G, Boutellier U: Further glycogen decrease during early recovery after eccentric exercise despite a high carbohydrate intake. Eur J Nutr. 2004 Jun;43(3):148-59. Epub 2004 Jan 6. Pubmed: 15168037
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID28087
HMDB IDHMDB00757
Pubchem Compound ID439177
Kegg IDC00182
ChemSpider ID388322
WikipediaGlycogen
BioCyc IDGlycogens
EcoCyc IDGlycogens

Enzymes

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:
malP
Uniprot ID:
P00490
Molecular weight:
90522
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
General function:
Involved in 1,4-alpha-glucan branching enzyme activity
Specific function:
Catalyzes the formation of the alpha-1,6-glucosidic linkages in glycogen by scission of a 1,4-alpha-linked oligosaccharide from growing alpha-1,4-glucan chains and the subsequent attachment of the oligosaccharide to the alpha-1,6 position. Has a preference for transferring chains of 5 to 16 glucose units
Gene Name:
glgB
Uniprot ID:
P07762
Molecular weight:
84336
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan chain to a primary hydroxy group in a similar glucan chain.
General function:
Involved in biosynthetic process
Specific function:
Synthesizes alpha-1,4-glucan chains using ADP-glucose
Gene Name:
glgA
Uniprot ID:
P0A6U8
Molecular weight:
52822
Reactions
ADP-glucose + (1,4-alpha-D-glucosyl)(n) = ADP + (1,4-alpha-D-glucosyl)(n+1).
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:
glgP
Uniprot ID:
P0AC86
Molecular weight:
93172
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the alpha-1,6-glucosidic linkages in glycogen which has first been partially depolymerized by phosphorylase. Shows only very little activity with native glycogen
Gene Name:
glgX
Uniprot ID:
P15067
Molecular weight:
73576