Identification
YMDB ID: YMDB00881
Name: Glycogen
Species: Saccharomyces cerevisiae
Strain: Baker's yeast
Description: Glycogen is a polysaccharide that is the principal storage form of glucose in animal and human cells.
Structure: Thumb
Download: MOL | SDF | SMILES | InChI
Synonyms:
  • Glycogen
  • Lyoglycogen
  • Phytoglycogen
Chemical Formula:
C24H42O21
Weight: Average: 666.5777
Monoisotopic: 666.221858406
InChI Key: InChIKey=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
Plain Text
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:
(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
SMILES:
[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OC([H])([H])[C@@]2([H])O[C@]([H])(O[C@@]3([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])O[C@]3([H])C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[C@@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Plain Text
Chemical Taxonomy
Kingdom: Organic Compounds
Super Class: Carbohydrates and Carbohydrate Conjugates
Class: Tetrasaccharides
Sub Class: Hexose Tetrasaccharides
Other Descriptors:
  • Organic Oxonium Compounds
  • Aliphatic Heteropolycyclic Compounds
Substituents:
  • pyran
  • secondary alcohol
  • hemiacetal
  • 1,2-diol
  • acetal
  • primary alcohol
Physical Properties
State: Solid
Charge: 0
Melting point: 270-280 °C
Experimental Properties: Not Available
Predicted Properties:
Property Value Source
Water Solubility: 3.43e+02 g/l ALOGPS
LogP: -2.67 ALOGPS
LogP: -8.245046155 ChemAxon Molconvert
LogS: -0.29 ALOGPS
pKa: 11.9 ChemAxon Molconvert
Hydrogen Acceptor Count: 21 ChemAxon Molconvert
Hydrogen Donor Count: 14 ChemAxon Molconvert
Polar Surface Area: 347.83 A2 ChemAxon Molconvert
Rotatable Bond Count: 10 ChemAxon Molconvert
Refractivity: 133.2 ChemAxon Molconvert
Polarizability: 60.5 ChemAxon Molconvert
Biological Properties
Cellular Locations:
  • vacuole
  • cytoplasm
Pathways: Not Available
Concentrations
Not Available
Details describing the conversion of literature concentrations can be found here.
Spectra
Experimental 13C HSQC Spectrum view
Experimental 1H NMR Spectrum view
Experimental 2D TOCSY Spectrum view
Experimental 13C NMR Spectrum view
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676. Pubmed: 21062828 Link_out
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160. Pubmed: 18846089 Link_out
  • Teste, M. A., Enjalbert, B., Parrou, J. L., Francois, J. M. (2000). "The Saccharomyces cerevisiae YPR184w gene encodes the glycogen debranching enzyme." FEMS Microbiol Lett 193:105-110. Pubmed: 11094287 Link_out
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71. Pubmed: 18687109 Link_out
  • Wang, Z., Wilson, W. A., Fujino, M. A., Roach, P. J. (2001). "Antagonistic controls of autophagy and glycogen accumulation by Snf1p, the yeast homolog of AMP-activated protein kinase, and the cyclin-dependent kinase Pho85p." Mol Cell Biol 21:5742-5752. Pubmed: 11486014 Link_out
Synthesis Reference: Parodi 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.
External Links:
Resource Link
CHEBI ID: 28087 Link_out
HMDB ID: HMDB00757 Link_out
Pubchem Compound ID: 439177 Link_out
Kegg ID: C00182 Link_out
Wikipedia: Glycogen Link_out
BioCyc ID: CPD0-971 Link_out
Enzymes
Name: Glycogen debranching enzyme
Reactions:
  • Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan.
  • Hydrolysis of (1->6)-alpha-D-glucosidic branch linkages in glycogen phosphorylase limit dextrin.
Gene Name: GDB1 Link_out
Uniprot ID: Q06625 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucoamylase, intracellular sporulation-specific
Reactions:
  • Hydrolysis of terminal (1->4)-linked alpha-D-glucose residues successively from non-reducing ends of the chains with release of beta-D-glucose.
Gene Name: SGA1 Link_out
Uniprot ID: P08019 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase
Reactions:
  • (1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
Gene Name: GPH1 Link_out
Uniprot ID: P06738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase isoform 2
Reactions:
  • UDP-glucose ((1->4)-alpha-D-glucosyl)(n) = UDP + ((1->4)-alpha-D-glucosyl)(n+1).
Gene Name: GSY2 Link_out
Uniprot ID: P27472 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase isoform 1
Reactions:
  • UDP-glucose ((1->4)-alpha-D-glucosyl)(n) = UDP + ((1->4)-alpha-D-glucosyl)(n+1).
Gene Name: GSY1 Link_out
Uniprot ID: P23337 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1,4-alpha-glucan-branching enzyme
Reactions:
  • Transfers a segment of a (1->4)-alpha-D-glucan chain to a primary hydroxy group in a similar glucan chain.
Gene Name: GLC3 Link_out
Uniprot ID: P32775 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Not Available