(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

• ChemBase ID: 177880
• Molecular Formular: C38H60O18
• Molecular Mass: 804.8722
• Monoisotopic Mass: 804.37796508
• SMILES: C1C[C@]([C@@H]2[C@@](C1)([C@H]1[C@]3(CC2)CC(=C)[C@](CC1)(C3)O[C@@H]1OC([C@H]([C@@H](C1O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO)O)O)CO)C)(C(=O)O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO)C
• Canonical SMILES: OCC1O[C@@H](O[C@@]23CC[C@@H]4[C@@](C2)(CC3=C)CC[C@H]2[C@@]4(C)CCC[C@@]2(C)C(=O)O[C@@H]2OC(CO)[C@H]([C@@H](C2O)O)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17?,18?,19?,20-,21-,22+,23+,24+,25-,26-,27-,28?,29?,30?,31-,32-,33-,35+,36+,37+,38-/m0/s1
• InChIKey: UEDUENGHJMELGK-PIICXALNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylate
• IUPAC Traditional name: (2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylate
• Synonyms: (4α)-13-[(2-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic Acid β-D-Glucopyranosyl Ester; Steviosin; α-G-Sweet; Stevioside

Database IDs

• CAS Number: 57817-89-7
• PubChem SID: 164233790
• PubChem CID: 71752245

CALCULATED PROPERTIES

• Acid pKa: 11.841073
• H Acceptors: 17
• H Donor: 11
• LogD (pH = 5.5): -2.1612086
• LogD (pH = 7.4): -2.1612241
• Log P: -2.1612084
• Molar Refractivity: 186.1495 cm^3
• Polarizability: 76.87828 Å^3
• Polar Surface Area: 294.98 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S686730

Stevioside is a glycoside from the stevia plant. Stevioside is a natural sweetening agent with sweetness about 250 times that of sugar with negligible effect on blood glucose. Stevioside, much like other steviol glycoside is known for its application in t

REFERENCES

• Mishra, P. et al.: Glob. J. Biotechnol. Biochem., 5, 62 (2010)
• Gregersen, S. et al.: Metab. Clin. Exp., 53, 73 (2010)
• Chan, P. et al.: Life Sci., 63, 1679 (2010)
• Heerranz-Lopez, M. et al.: Agro Food Ind. Hi-Tech, 21, 38 (2010)