Sucrose (PAMDB000109)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000109
Identification
Name: Sucrose
Description:Sucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. Sucrose can be used as a carbon/energy substrate by Pseudomonas aeruginosa. The sucrose porin (ScrY) which resides in the bacterial outer membrane facilitate the passive diffusion of sucrose into the cell. Sucrose metabolism is controlled by the csc regulon. The csc regulon comprises three genes for a sucrose permease, a fructokinase, and a sucrose hydrolase (genes cscB, cscK, and cscA, respectively).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-D-glucopyranosyl β-D-fructofuranoside
  • (+)-Sucrose
  • a-D-Glucopyranosyl b-D-fructofuranoside
  • Alpha-D-Glucopyranosyl beta-D-fructofuranoside
  • B -D-Fructofuranosyl a-D-glucopyranoside
  • D-(+)-Saccharose
  • D-(+)-Sucrose
  • D-Sucrose
  • Glc(α1->2β)Fru
  • GLC(a1->2b)fru
  • Glc(alpha1->2beta)Fru
  • GLC(α1->2β)fru
  • Saccharose
  • Saccharum
  • Sucrose
  • Sugar
  • Table sugar
  • White sugar
  • α-D-Glucopyranosyl β-D-fructofuranoside
Chemical Formula: C12H22O11
Average Molecular Weight: 342.2965
Monoisotopic Molecular Weight: 342.116211546
InChI Key: CZMRCDWAGMRECN-UGDNZRGBSA-N
InChI:InChI=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
CAS number: 57-50-1
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 Name: sucrose
SMILES:OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent O-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • C-glycosyl compound
  • Oxane
  • Oxolane
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 185.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:2100.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.70 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility824.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.77 m3·mol-1ChemAxon
Polarizability31.03 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphate
Sucrose + Water <> D-Fructose + D-Glucose
Sucrose + Water <> beta-D-Fructose + alpha-D-Glucose
Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate
Protein EIIB N(pi)-phospho-L-histidine/cysteine + Sucrose > protein EIIB + sugar phosphate
Sugar phosphate + Water > Sucrose + Inorganic phosphate
Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate
Sucrose + Water <> D-Fructose + D-Glucose + D-Fructose
UDP-Glucose + D-Fructose + D-Fructose <> Sucrose + Phosphate
D-Fructose + Alpha-D-glucose 1-phosphate + D-Fructose <> Phosphate + Sucrose
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0gba-0930000000-594ae5d59d217235e6c7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-02ta-0932000000-8fa2c23f886fb0c63312View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9731000000-0d702b863a0419bd559cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-1ba130720abffe5e93d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-9600000000-bf4df12e3ec24b4de57bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9100000000-5308faa0508d0796ef2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-9804000000-018a029ba3843a8db2bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-05dm-9100000000-ff1c60103a4253a94cf7View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73. Pubmed: 12948025
  • Calderilla-Fajardo SB, Cazares-Delgadillo J, Villalobos-Garcia R, Quintanar-Guerrero D, Ganem-Quintanar A, Robles R: Influence of sucrose esters on the in vivo percutaneous penetration of octyl methoxycinnamate formulated in nanocapsules, nanoemulsion, and emulsion. Drug Dev Ind Pharm. 2006 Jan;32(1):107-13. Pubmed: 16455609
  • Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7. Pubmed: 3546377
  • Chanarat P, Chiewsilp P: A simple method for the elimination of platelets from the lymphocyte-platelet mixture by sucrose. Am J Clin Pathol. 1975 Feb;63(2):237-9. Pubmed: 803775
  • Cohen J, Malter H, Wright G, Kort H, Massey J, Mitchell D: Partial zona dissection of human oocytes when failure of zona pellucida penetration is anticipated. Hum Reprod. 1989 May;4(4):435-42. Pubmed: 2745674
  • Giofre MR, Meduri G, Pallio S, Calandra S, Magnano A, Niceforo D, Cinquegrani M, di Leo V, Mazzon E, Sturniolo GC, Longo G, Fries W: Gastric permeability to sucrose is increased in portal hypertensive gastropathy. Eur J Gastroenterol Hepatol. 2000 May;12(5):529-33. Pubmed: 10833096
  • Hamer I, Jadot M: Endolysosomal transport of newly-synthesized cathepsin D in a sucrose model of lysosomal storage. Exp Cell Res. 2005 Oct 1;309(2):284-95. Pubmed: 16055118
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57. Pubmed: 9154994
  • Nakano S, Kato T, Nakamura S, Kameyama M: Acetylcholinesterase activity in cerebrospinal fluid of patients with Alzheimer's disease and senile dementia. J Neurol Sci. 1986 Sep;75(2):213-23. Pubmed: 3760912
  • Ponec M, Wauben-Penris PJ, Burger A, Kempenaar J, Bodde HE: Nitroglycerin and sucrose permeability as quality markers for reconstructed human epidermis. Skin Pharmacol. 1990;3(2):126-35. Pubmed: 2127677
  • Poschalko A, Rohr T, Gruber H, Bianco A, Guichard G, Briand JP, Weber V, Falkenhagen D: SUBPOL: a novel SUcrose-Based Polymer support for solid-phase peptide synthesis and affinity chromatography applications. J Am Chem Soc. 2003 Nov 5;125(44):13415-26. Pubmed: 14583037
  • Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7. Pubmed: 16187674
  • Rogers AJ, Greenwald MH, Deguzman MA, Kelley ME, Simon HK: A randomized, controlled trial of sucrose analgesia in infants younger than 90 days of age who require bladder catheterization in the pediatric emergency department. Acad Emerg Med. 2006 Jun;13(6):617-22. Epub 2006 Apr 24. Pubmed: 16636358
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Skogsdal Y, Eriksson M, Schollin J: Analgesia in newborns given oral glucose. Acta Paediatr. 1997 Feb;86(2):217-20. Pubmed: 9055897
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Wilson M, Patel H, Kpendema H, Noar JH, Hunt NP, Mordan NJ: Corrosion of the intra-oral magnets by multi-species biofilms in the presence and absence of sucrose. Biomaterials. 1997 Jan;18(1):53-7. Pubmed: 9003897
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17992
HMDB IDHMDB00258
Pubchem Compound ID5988
Kegg IDC00089
ChemSpider ID5768
WikipediaSucrose
BioCyc IDSUCROSE
EcoCyc IDSUCROSE
Ligand ExpoSUC

Enzymes

Protein Details
• PTS system N-acetylglucosamine-specific EIICBA component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylglucosamine transport
Gene Name:
nagE
Locus Tag:
PA3761
Molecular weight:
60.6 kDa
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
• PTS system fructose-specific EIIBC component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in fructose transport
Gene Name:
fruA
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
• Galactitol-specific phosphotransferase enzyme IIB component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatB
Locus Tag:
PA4484
Molecular weight:
53.1 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Transporters

Protein Details
• PTS system N-acetylglucosamine-specific EIICBA component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylglucosamine transport
Gene Name:
nagE
Locus Tag:
PA3761
Molecular weight:
60.6 kDa
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
• PTS system fructose-specific EIIBC component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in fructose transport
Gene Name:
fruA
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.