(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carbonyloxy]oxane-2-carboxylic acid

• ChemBase ID: 171980
• Molecular Formular: C26H38O9
• Molecular Mass: 494.57452
• Monoisotopic Mass: 494.2515828
• SMILES: C1C[C@]([C@@H]2[C@@](C1)([C@H]1[C@]3(CC2)C[C@](CC1)(C(=O)C3)C)C)(C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)[C@]2(C)CCC[C@@]3([C@@H]2CC[C@]24[C@H]3CC[C@@](C4)(C(=O)C2)C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C26H38O9/c1-23-9-5-14-24(2)7-4-8-25(3,13(24)6-10-26(14,12-23)11-15(23)27)22(33)35-21-18(30)16(28)17(29)19(34-21)20(31)32/h13-14,16-19,21,28-30H,4-12H2,1-3H3,(H,31,32)/t13-,14-,16-,17-,18+,19-,21-,23-,24+,25+,26-/m0/s1
• InChIKey: HIZZTUWFGBYLHI-QNMZKQGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carbonyloxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carbonyloxy]oxane-2-carboxylic acid
• Synonyms: 1-[(4α)-13-Methyl-16-oxo-17-norkauran-18-oate]-β-D-glucopyranuronic Acid; Isosteviol Glucuronide; Isosteviol Acyl-β-D-glucuronide

Database IDs

• CAS Number: 1080018-94-5
• PubChem SID: 164227890
• PubChem CID: 71749636

CALCULATED PROPERTIES

• Acid pKa: 3.3583503
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.42608196
• LogD (pH = 7.4): -0.85965073
• Log P: 2.5534277
• Molar Refractivity: 120.5044 cm^3
• Polarizability: 49.039024 Å^3
• Polar Surface Area: 150.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I902210

A metabolite of Isosteviol (I902200).

REFERENCES

• Wu, Ya., et al.: Bioorg. Med. Chem., 17, 1464 (2009)