(2R,3S,4R,5R,6S)-2-{[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 2489
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: OC[C@@H]1O[C@H](O[C@@]2(CO)O[C@@H](CO)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]1O[C@]([C@@H]([C@H]1O)O)(CO)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O
• 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+/m0/s1
• InChIKey: CZMRCDWAGMRECN-MTNNYNCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,6S)-2-{[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: @sucrose
• Synonyms: Sucrose

Database IDs

• CAS Number: 57-50-1
• PubChem SID: 46506134; 160965939
• PubChem CID: 46936484

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.84128
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.5288353
• LogD (pH = 7.4): -4.5288506
• Log P: -4.528835
• Molar Refractivity: 68.7741 cm^3
• Polarizability: 28.969793 Å^3
• Polar Surface Area: 189.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.63
• LOG S: 0.38
• Solubility (Water): 8.24e+02 g/l

PROPERTIES

Physical Property

• Solubility: 2100 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): -3.70 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB02772

• Drug Groups: experimental
• Description: 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. [PubChem]
• References: Ten S, Maclaren N: Insulin resistance syndrome in children. J Clin Endocrinol Metab. 2004 Jun;89(6):2526-39. [Pubmed] ; Aguilera AA, Diaz GH, Barcelata ML, Guerrero OA, Ros RM: Effects of fish oil on hypertension, plasma lipids, and tumor necrosis factor-alpha in rats with sucrose-induced metabolic syndrome. J Nutr Biochem. 2004 Jun;15(6):350-7. [Pubmed] ; Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H: Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats. Exp Biol Med (Maywood). 2004 Jun;229(6):486-93. [Pubmed] ; Lombardo YB, Drago S, Chicco A, Fainstein-Day P, Gutman R, Gagliardino JJ, Gomez Dumm CL: Long-term administration of a sucrose-rich diet to normal rats: relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas. Metabolism. 1996 Dec;45(12):1527-32. [Pubmed]
• External Links: Wikipedia; RxList

REFERENCES

• Ten S, Maclaren N: Insulin resistance syndrome in children. J Clin Endocrinol Metab. 2004 Jun;89(6):2526-39. Pubmed
• Aguilera AA, Diaz GH, Barcelata ML, Guerrero OA, Ros RM: Effects of fish oil on hypertension, plasma lipids, and tumor necrosis factor-alpha in rats with sucrose-induced metabolic syndrome. J Nutr Biochem. 2004 Jun;15(6):350-7. Pubmed
• Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H: Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats. Exp Biol Med (Maywood). 2004 Jun;229(6):486-93. Pubmed
• Lombardo YB, Drago S, Chicco A, Fainstein-Day P, Gutman R, Gagliardino JJ, Gomez Dumm CL: Long-term administration of a sucrose-rich diet to normal rats: relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas. Metabolism. 1996 Dec;45(12):1527-32. Pubmed