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Identification
YMDB IDYMDB00906
NameSucrose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSucrose, also known as cane sugar or saccharose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Sucrose is an extremely weak basic (essentially neutral) compound (based on its pKa). Sucrose exists in all living species, ranging from bacteria to humans. sucrose can be converted into β-D-fructofuranose and α-D-glucose; which is catalyzed by the enzyme invertase. In yeast, sucrose is involved in the metabolic pathway called the fructose metabolism pathway.
Structure
Thumb
Synonyms
  • (+)-Sucrose
  • b -D-Fructofuranosyl a-D-glucopyranoside
  • D-(+)-Saccharose
  • D-(+)-Sucrose
  • D-Sucrose
  • Saccharose
  • Saccharum
  • Sucrose
  • Sugar
  • Table sugar
  • White sugar
  • 1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranoside
  • beta-D-Fruf-(21)-alpha-D-GLCP
  • Cane sugar
  • Sacarosa
  • Sacharose
  • White soft sugar
  • Sugar, compressible
  • Sugar, confectioner's
  • Sugar spheres
  • Sucrose, purified
  • 1-a-D-Glucopyranosyl-2-b-D-fructofuranoside
  • 1-Α-D-glucopyranosyl-2-β-D-fructofuranoside
  • b-D-Fruf-(21)-a-D-GLCP
  • Β-D-fruf-(21)-α-D-GLCP
CAS number57-50-1
WeightAverage: 342.2965
Monoisotopic: 342.116211546
InChI KeyCZMRCDWAGMRECN-UGDNZRGBSA-N
InChIInChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Namesucrose
Chemical FormulaC12H22O11
SMILES[H]OC([H])([H])[C@@]1([H])O[C@](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])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • C-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point185.5 °C
Experimental Properties
PropertyValueReference
Water Solubility2100 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.70 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility824 g/LALOGPS
logP-2.6ALOGPS
logP-4.5ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.77 m³·mol⁻¹ChemAxon
Polarizability31.04 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Galactose metabolismec00052 Map00052
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Sucrose + waterD-Fructose + Alpha-D-Glucose
Alpha-D-Glucose + D-FructoseSucrose + water
KEGG Reactions
water + Sucrose D-Fructose + D-Glucose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0gba-0930000000-594ae5d59d217235e6c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-02ta-0932000000-8fa2c23f886fb0c63312JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9731000000-0d702b863a0419bd559cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-594ae5d59d217235e6c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02ta-0932000000-8fa2c23f886fb0c63312JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9731000000-0d702b863a0419bd559cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i01-0932000000-a84ab9868385a177391aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nt9-9576000000-4af9cf7cb58154231f7bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-8750249000-757f1c653f998599ba0bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-1ba130720abffe5e93d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-9600000000-bf4df12e3ec24b4de57bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9100000000-5308faa0508d0796ef2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-9804000000-018a029ba3843a8db2bdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-9804000000-018a029ba3843a8db2bdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-61fdb02b67338e94c2a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-3b225ec11ada7061156bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9700000000-18b83ffd2452e8f7420dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-1901000000-b27bed8dffbc1fa29601JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-0900000000-85fe4d893cc72a297745JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-8900000000-7ee1d127314574cf8eecJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-05dm-9100000000-ff1c60103a4253a94cf7JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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-D676.21062828
  • 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 26:1155-1160.18846089
  • Fukushima, E., Arata, Y., Endo, T., Sonnewald, U., Sato, F. (2001). "Improved salt tolerance of transgenic tobacco expressing apoplastic yeast-derived invertase." Plant Cell Physiol 42:245-249.11230581
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Fitremann, Juliette; Queneau, Yves; Maitre, Jean-Paul; Bouchu, Alain. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Letters (2007), 48(23), 4111-4114.
External Links:
ResourceLink
CHEBI ID17992
HMDB IDHMDB00258
Pubchem Compound ID5988
Kegg IDC00089
ChemSpider ID24607894
FOODB IDFDB003715
WikipediaSucrose
BioCyc IDSUCROSE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalytic subunit of glucosidase 2, which cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins
Gene Name:
ROT2
Uniprot ID:
P38138
Molecular weight:
110265.0
Reactions
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC1
Uniprot ID:
P10594
Molecular weight:
60569.89844
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC3
Uniprot ID:
P10595
Molecular weight:
8649.90039
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC4
Uniprot ID:
P10596
Molecular weight:
60574.80078
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC5
Uniprot ID:
P10597
Molecular weight:
8649.90039
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC2
Uniprot ID:
P00724
Molecular weight:
60638.89844
Reactions
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC7
Uniprot ID:
P07635
Molecular weight:
11248.90039