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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:57:57 UTC
NP-MRD IDNP0000229
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlycogen
DescriptionGlycogen is a highly-branched polymer of about 30,000 glucose residues. The simplest structure of glycogen is made up of four units of glucose with an approximate molecular weight of 666 daltons. However, large molecules of glycogen can reach molecular weights in the order of 5 million Da. Most of the glucose units are linked together by alpha-1,4 glycosidic bonds, and approximately 1 in 12 glucose residues also form a 1,6 glycosidic bond with a second glucose, resulting 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 necessary glycogenolysis to take place 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 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 Mass666.5777 Da
Monoisotopic Mass666.22186 Da
IUPAC Name(2R,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}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,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}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Eubacteria
  • Fungi
  • 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
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point270 - 280 °CNot Available
    Boiling Point1027.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
    Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogP-5.590 (est)The Good Scents Company Information System
    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
    Polarizability61.39 ųChemAxon
    Number of Rings4ChemAxon
    BioavailabilityNoChemAxon
    Rule of FiveNoChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleYesChemAxon
    External Links
    HMDB IDHMDB0000757
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022227
    KNApSAcK IDNot Available
    Chemspider ID388322
    KEGG Compound IDC00182
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkGlycogen
    METLIN ID160
    PubChem Compound439177
    PDB IDNot Available
    ChEBI ID28087
    Good Scents IDrw1233951
    References
    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 ]