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Record Information
Version1.0
Creation Date2016-07-13 19:42:46 UTC
Update Date2016-07-20 20:56:41 UTC
LmdbLMDB00119
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
White soft sugarKegg
Sugar, compressibleKegg
Sugar, confectioner'sKegg
Sugar spheresKegg
Sucrose, purifiedKegg
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 KeyCZMRCDWAGMRECN-UGDNZRGBSA-N
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-0930000000-594ae5d59d217235e6c7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-02ta-0932000000-8fa2c23f886fb0c63312Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9731000000-0d702b863a0419bd559cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-594ae5d59d217235e6c7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02ta-0932000000-8fa2c23f886fb0c63312Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9731000000-0d702b863a0419bd559cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i01-0932000000-a84ab9868385a177391aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nt9-9576000000-4af9cf7cb58154231f7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-8750249000-757f1c653f998599ba0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-1ba130720abffe5e93d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-9600000000-bf4df12e3ec24b4de57bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9100000000-5308faa0508d0796ef2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-9804000000-018a029ba3843a8db2bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-9804000000-018a029ba3843a8db2bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9500000000-292e67f588f0d531ef65Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-2709000000-0e3c703e04384a1e3293Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ef17557045affea2bd08Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-20fcddbd8c975ed3b6deSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0040-0591000000-7087bb9a939bd10f818aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000j-8900000000-9332c87e291ba54d3cbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-7744e4ab4fd78c24407fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0b9o-9404000000-1d981db61b2f46503e23Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ot-3920000000-4cba5c16114c58b38f7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0v5a-7890000000-69957548042f63c9dd84Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-4390000000-0d6a0896805d60fa3f2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052r-9300000000-a1b937218ce647359fdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000f-6907000000-2f97793cff75b6ba35a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-9100000000-eb237dfae067794baf48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-61fdb02b67338e94c2a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-3b225ec11ada7061156bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9700000000-18b83ffd2452e8f7420dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-1901000000-b27bed8dffbc1fa29601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-0900000000-85fe4d893cc72a297745Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-8900000000-7ee1d127314574cf8eecSpectrum
MSMass Spectrum (Electron Ionization)splash10-05dm-9100000000-ff1c60103a4253a94cf7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB02772
HMDB IDHMDB0000258
FooDB IDFDB003715
Phenol Explorer IDNot Available
KNApSAcK IDC00001151
BiGG IDNot Available
BioCyc IDSUCROSE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSucrose
Chemspider IDNot Available
ChEBI ID17992
PubChem Compound ID5988
Kegg Compound IDC00089
YMDB IDYMDB00906
ECMDB IDECMDB00258
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available