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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:49:15 UTC
HMDB IDHMDB0000757
Secondary Accession Numbers
  • HMDB00757
Metabolite Identification
Common NameGlycogen
DescriptionGlycogen is a highly-branched polymer of about 30,000 glucose residues and has a molecular weight between 106 and 107 daltons (4.8 million approx.). Most of Glc units are linked by alpha-1,4 glycosidic bonds, approximately 1 in 12 Glc residues also makes -1,6 glycosidic bond with a second Glc which results in the creation of a branch. 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. In hypoglycemia caused by excessive insulin, liver glycogen levels are high, but the high insulin level prevents the glycogenolysis necessary to maintain normal blood sugar levels. Glucagon is a common treatment for this type of hypoglycemia. Glycogen is a polysaccharide that is the principal storage form of glucose (Glc) in animal and human cells. Glycogen is found in the form of granules in the cytosol in many cell types. Hepatocytes (liver cells) have the highest concentration of it - up to 8% of the fresh weight in well fed state, or 100 to 120 g in an adult - giving liver a distinctive, 'starchy taste'. In the muscles, glycogen is found in a much lower concentration (1% of the muscle mass), but the total amount exceeds that in liver. Small amounts of glycogen are found in the kidneys, and even smaller amounts in certain glial cells in the brain and white blood cells.
Structure
Thumb
Synonyms
ValueSource
Animal starchHMDB
Liver starchHMDB
LyoglycogenHMDB
PhytoglycogenHMDB
Chemical FormulaC24H42O21
Average Molecular Weight666.5777
Monoisotopic Molecular Weight666.221858406
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 Nameglycogen
CAS Registry Number9005-79-2
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
InChI Identifier
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
InChI KeyBYSGBSNPRWKUQH-UJDJLXLFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Cell:

    Element:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 - 280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB/PathwhizKEGG
Glycogen synthetase deficiencyPw000528Pw000528 greyscalePw000528 simpleNot Available
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisPw000529Pw000529 greyscalePw000529 simpleNot Available
Glycogenosis, Type IV. Amylopectinosis, Anderson diseasePw000530Pw000530 greyscalePw000530 simpleNot Available
Glycogenosis, Type VI. Hers diseasePw000531Pw000531 greyscalePw000531 simpleNot Available
Mucopolysaccharidosis VI. Sly syndromePw000532Pw000532 greyscalePw000532 simpleNot Available
Displaying entries 1 - 5 of 7 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified39.1 +/- 3.1 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified43.3 +/- 3.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00509
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022227
    KNApSAcK IDNot Available
    Chemspider ID388322
    KEGG Compound IDC00182
    BioCyc IDCPD0-971
    BiGG IDNot Available
    Wikipedia LinkGlycogen
    METLIN ID160
    PubChem Compound439177
    PDB IDNot Available
    ChEBI ID28087
    References
    Synthesis ReferenceParodi A J; Krisman C R; Mordoh J In vitro synthesis of particulate glycogen from uridine diphosphate glucose. II. Some studies on the growth process. Archives of biochemistry and biophysics (1970), 141(1), 219-27.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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 ]
    2. 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 ]
    3. 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 (1985). 2005 Aug;99(2):707-14. Epub 2005 Apr 14. [PubMed:15831796 ]
    4. 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 ]
    5. 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 ]
    6. Jentjens R, Jeukendrup A: Determinants of post-exercise glycogen synthesis during short-term recovery. Sports Med. 2003;33(2):117-44. [PubMed:12617691 ]
    7. 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 ]
    8. 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 ]
    9. 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 ]
    10. 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 ]
    11. 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 ]
    12. 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 ]
    13. 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 ]
    14. 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 ]
    15. 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 ]
    16. 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 ]
    17. 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 ]
    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 ]
    19. 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 ]
    20. 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 ]

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
    Gene Name:
    AGL
    Uniprot ID:
    P35573
    Molecular weight:
    Not Available
    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 transferase activity, transferring glycosyl groups
    Specific function:
    Self-glucosylates, via an inter-subunit mechanism, to form an oligosaccharide primer that serves as substrate for glycogen synthase.
    Gene Name:
    GYG2
    Uniprot ID:
    O15488
    Molecular weight:
    51998.955
    General function:
    Involved in hydrolase activity
    Specific function:
    Protein phosphatase that associates with over 200 regulatory proteins to form highly specific holoenzymes which dephosphorylate hundreds of biological targets. Protein phosphatase (PP1) is essential for cell division, it participates in the regulation of glycogen metabolism, muscle contractility and protein synthesis. Involved in regulation of ionic conductances and long-term synaptic plasticity. Component of the PTW/PP1 phosphatase complex, which plays a role in the control of chromatin structure and cell cycle progression during the transition from mitosis into interphase.
    Gene Name:
    PPP1CB
    Uniprot ID:
    P62140
    Molecular weight:
    37186.45
    General function:
    Involved in carbohydrate binding
    Specific function:
    Dual specificity protein phosphatase. May be involved in the control of glycogen metabolism, particularly in monitoring for and preventing the formation of poorly branched glycogen molecules (polyglucosans). Acts as a scaffold protein to facilitate PPP1R3C/PTG ubiquitination by NHLRC1/malin. Forms a complex with NHLRC1/malin and HSP70 and this complex suppresses the cellular toxicity of misfolded proteins by promoting their degradation through the ubiquitin-proteasome system (UPS). Isoform 2, an inactive phosphatase, could function as a dominant-negative regulator for the phosphatase activity of isoform 1.
    Gene Name:
    EPM2A
    Uniprot ID:
    O95278
    Molecular weight:
    35518.41
    General function:
    Involved in hydrolase activity
    Specific function:
    Protein phosphatase that associates with over 200 regulatory proteins to form highly specific holoenzymes which dephosphorylate hundreds of biological targets. Protein phosphatase 1 (PP1) is essential for cell division, and participates in the regulation of glycogen metabolism, muscle contractility and protein synthesis. Dephosphorylates RPS6KB1. Involved in regulation of ionic conductances and long-term synaptic plasticity. May play an important role in dephosphorylating substrates such as the postsynaptic density-associated Ca(2+)/calmodulin dependent protein kinase II. Component of the PTW/PP1 phosphatase complex, which plays a role in the control of chromatin structure and cell cycle progression during the transition from mitosis into interphase.
    Gene Name:
    PPP1CC
    Uniprot ID:
    P36873
    Molecular weight:
    38517.92
    General function:
    Involved in catalytic activity
    Specific function:
    Not Available
    Gene Name:
    AMY1A
    Uniprot ID:
    P04745
    Molecular weight:
    Not Available
    General function:
    Involved in catalytic activity
    Specific function:
    May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
    Gene Name:
    MGAM
    Uniprot ID:
    O43451
    Molecular weight:
    Not Available
    General function:
    Involved in catalytic activity
    Specific function:
    Not Available
    Gene Name:
    Not Available
    Uniprot ID:
    Q59ET0
    Molecular weight:
    86112.7
    General function:
    Involved in hydrolase activity
    Specific function:
    Protein phosphatase that associates with over 200 regulatory proteins to form highly specific holoenzymes which dephosphorylate hundreds of biological targets. Protein phosphatase 1 (PP1) is essential for cell division, and participates in the regulation of glycogen metabolism, muscle contractility and protein synthesis. Involved in regulation of ionic conductances and long-term synaptic plasticity. May play an important role in dephosphorylating substrates such as the postsynaptic density-associated Ca(2+)/calmodulin dependent protein kinase II. Component of the PTW/PP1 phosphatase complex, which plays a role in the control of chromatin structure and cell cycle progression during the transition from mitosis into interphase. Regulates NEK2 function in terms of kinase activity and centrosome number and splitting, both in the presence and absence of radiation-induced DNA damage. Regulator of neural tube and optic fissure closure, and enteric neural crest cell (ENCCs) migration during development.
    Gene Name:
    PPP1CA
    Uniprot ID:
    P62136
    Molecular weight:
    38630.99
    General function:
    Involved in protein serine/threonine phosphatase activity
    Specific function:
    Acts as a glycogen-targeting subunit for PP1 and regulates its activity. Activates glycogen synthase, reduces glycogen phosphorylase activity and limits glycogen breakdown. Dramatically increases basal and insulin-stimulated glycogen synthesis upon overexpression in a variety of cell types
    Gene Name:
    PPP1R3C
    Uniprot ID:
    Q9UQK1
    Molecular weight:
    36445.2
    General function:
    Involved in glycogen metabolic process
    Specific function:
    Acts as a glycogen-targeting subunit for phosphatase PP1. Facilitates interaction of the PP1 with enzymes of the glycogen metabolism and regulates its activity. Suppresses the rate at which PP1 dephosphorylates (inactivates) glycogen phosphorylase and enhances the rate at which it activates glycogen synthase and therefore limits glycogen breakdown. Its activity is inhibited by PYGL, resulting in inhibition of the glycogen synthase and glycogen phosphorylase phosphatase activities of PP1. Dramatically increases basal and insulin-stimulated glycogen synthesis upon overexpression in hepatocytes
    Gene Name:
    PPP1R3B
    Uniprot ID:
    Q86XI6
    Molecular weight:
    32694.9