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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:26 UTC
HMDB IDHMDB00258
Secondary Accession NumbersNone
Metabolite Identification
Common NameSucrose
DescriptionSucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is derived by crushing and extraction of sugarcane (Saccharum officinarum) with water or extraction of the sugar beet (Beta vulgaris) with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is wiidespread in seeds, leaves, fruits, flowers and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons mainly from the juice of sugar cane (20%) and sugar beet (17%). In addition to its use as a sweetner, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer and thickening agent.
Structure
Thumb
Synonyms
ValueSource
1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranosideChEBI
beta-D-Fruf-(21)-alpha-D-GLCPChEBI
Cane sugarChEBI
SacarosaChEBI
SaccharoseChEBI
SacharoseChEBI
Table sugarChEBI
White sugarChEBI
1-a-D-Glucopyranosyl-2-b-D-fructofuranosideGenerator
1-α-D-glucopyranosyl-2-β-D-fructofuranosideGenerator
b-D-Fruf-(21)-a-D-GLCPGenerator
β-D-fruf-(21)-α-D-GLCPGenerator
(+)-SucroseHMDB
b -D-Fructofuranosyl a-D-glucopyranosideHMDB
D-(+)-SaccharoseHMDB
D-(+)-SucroseHMDB
D-SucroseHMDB
SaccharumHMDB
SugarHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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 Namesucrose
CAS Registry Number57-50-1
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
InChI Identifier
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
InChI KeyInChIKey=CZMRCDWAGMRECN-UGDNZRGBSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentO-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2100.0 mg/mLNot Available
LogP-3.70HANSCH,C ET AL. (1995)
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
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
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Mouth
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Glycogen synthetase deficiencySMP00552Not Available
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisSMP00553Not Available
Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseSMP00554Not Available
Glycogenosis, Type VI. Hers diseaseSMP00555Not Available
Mucopolysaccharidosis VI. Sly syndromeSMP00556Not Available
Starch and Sucrose MetabolismSMP00058map00500
Sucrase-isomaltase deficiencySMP00557Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.8 +/- 1.2 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified1-113 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified52 (<1-309496) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified24 (<1-145076) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified1-6189 uMAdult (>18 years old)Female
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified1-26998 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-228 uMAdult (>18 years old)Male
normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified7.12 +/- 3.23 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.6055 (0-9.211) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified18.79 +/- 29.28 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified26.261 +/- 21.585 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified7.4 (1.4-19.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Cryptosporidium infection
details
UrineDetected and Quantified11 (0-159) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified19.126 +/- 34.203 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [22157537 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001131
KNApSAcK IDC00001151
Chemspider ID5768
KEGG Compound IDC00089
BioCyc IDSUCROSE
BiGG ID33807
Wikipedia LinkSucrose
NuGOwiki LinkHMDB00258
Metagene LinkHMDB00258
METLIN ID137
PubChem Compound5988
PDB IDSUC
ChEBI ID17992
References
Synthesis ReferenceFitremann, 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)
General References
  1. 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. [19212411 ]
  2. 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. [2026685 ]
  3. 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. [3546377 ]
  4. 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. [12948025 ]
  5. 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. [16636358 ]
  6. 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. [3760912 ]
  7. 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. [2127677 ]
  8. 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. [16187674 ]
  9. 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. [9154994 ]
  10. 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. [16455609 ]
  11. 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. [14583037 ]
  12. 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. [16055118 ]
  13. 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. [9003897 ]
  14. 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. [10833096 ]
  15. 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. [803775 ]
  16. Skogsdal Y, Eriksson M, Schollin J: Analgesia in newborns given oral glucose. Acta Paediatr. 1997 Feb;86(2):217-20. [9055897 ]
  17. 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. [2745674 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available
Reactions
Sucrose + Water → D-Fructose + D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
Reactions
Raffinose + Water → Beta-D-Galactose + Sucrosedetails
General function:
Involved in catalytic activity
Specific function:
Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name:
GAA
Uniprot ID:
P10253
Molecular weight:
Not Available
Reactions
Sucrose + Water → D-Fructose + D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
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
Reactions
Sucrose + Water → D-Fructose + D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
General function:
Involved in catalytic activity
Specific function:
Has alpha-glucosidase activity.
Gene Name:
GANC
Uniprot ID:
Q8TET4
Molecular weight:
Not Available
Reactions
Sucrose + Water → D-Fructose + D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails