(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-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 hydrate

• ChemBase ID: 153996
• Molecular Formular: C38H62O19
• Molecular Mass: 822.88748
• Monoisotopic Mass: 822.38852976
• SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]13[C@H]2CC[C@](C1)(C(=C)C3)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)(C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O.O
• Canonical SMILES: OC[C@H]1O[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]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O.O
• InChI: InChI=1S/C38H60O18.H2O/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;1H2/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+;/m1./s1
• InChIKey: FVECWZKNZGXJJO-QMYNVHDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-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 hydrate
• IUPAC Traditional name: stevioside hydrate
• Synonyms: (4α-13-[(2-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-D-glucopyranosyl ester; Stevioside hydrate; Stevioside

Database IDs

• CAS Number: 57817-89-7(anhydrous)
• PubChem SID: 162248135
• PubChem CID: 67350109

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

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Biological Source: from Stevia sp.
• Empirical Formula (Hill Notation): C38H60O18 · xH2O

DETAILS

Sigma Aldrich - S3572

Biochem/physiol Actions
Stevioside is a noncaloric natural sweetener, 300 times more potent than sucrose. It inhibits transepithelial transport of p-aminohippurate (PAH) by interfering with the organic anion transport system. At 0.5-1 mM, it showed no interaction with any organic anion transporters (OAT).