(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,4S,5R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(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: 177387
• Molecular Formular: C44H70O23
• Molecular Mass: 967.0128
• Monoisotopic Mass: 966.4307885
• 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[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO)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[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18?,19?,20?,21?,22-,23-,24+,25+,26+,27+,28-,29-,30-,31?,32?,33?,34-,35?,36-,37-,38-,39-,41+,42+,43+,44-/m0/s1
• InChIKey: HELXLJCILKEWJH-SQFYRQPJSA-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,5R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(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,5R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(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-[(O-β-D-Glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic Acid β-D-Glucopyranosyl Ester; 4G-S; Glycoside A3, from Stevia rebaudiana; Glycoside X; Pure Via; Reb-A 97; Rebiana; Sooolite!-Pure; Stevioside a3; Sweetener 4G-S; Rebaudioside A

Database IDs

• CAS Number: 58543-16-1
• PubChem SID: 164233297
• PubChem CID: 71751991

CALCULATED PROPERTIES

• Acid pKa: 11.750304
• H Acceptors: 22
• H Donor: 14
• LogD (pH = 5.5): -3.9320443
• LogD (pH = 7.4): -3.9320633
• Log P: -3.932044
• Molar Refractivity: 218.5628 cm^3
• Polarizability: 90.66092 Å^3
• Polar Surface Area: 374.13 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R139500

Rebaudioside A is a glycoside from the stevia plant. Rebaudioside A is used as a sweetener with sweetness about 300 times that of sugar with negligible effect on blood glucose. As a result, Rebaudioside A is known for its application in treatment of many

REFERENCES

• Mishra, P. et al.: Glob. J. Biotechnol. Biochem., 5, 62 (2010)
• Liu, J. et al.: Ship. Gong. Keji, 30, 359 (2010)
• Santini, A. et al.: Prog. Nutrit., 10, 5 (2010)
• Heerranz-Lopez, M. et al.: Agro Food Ind. Hi-Tech, 21, 38 (2010)