(2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177769
• Molecular Formular: C31H48O12
• Molecular Mass: 612.70562
• Monoisotopic Mass: 612.31457698
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OC(=O)C[C@@H](C[C@@H](CC[C@@H]1[C@H]2[C@H](C[C@H](C=C2C=C[C@@H]1C)C)OC(=O)C(CC)(C)C)O)O
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)O)O)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C31H48O12/c1-6-31(4,5)30(40)41-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(32)13-19(33)14-22(34)42-29-26(37)24(35)25(36)27(43-29)28(38)39/h7-8,11,15-16,18-21,23-27,29,32-33,35-37H,6,9-10,12-14H2,1-5H3,(H,38,39)/t15-,16-,18+,19+,20-,21-,23-,24+,25+,26-,27+,29-/m0/s1
• InChIKey: PBLYTKVVBICSHZ-ZPWRVAAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(βR,δR,1S,2S,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoate] β-D-Glucopyranuronic Acid; Simvastatin Acyl-β-D-glucuronide

Database IDs

• CAS Number: 463962-56-3
• PubChem SID: 164233679
• PubChem CID: 71752199

CALCULATED PROPERTIES

• Acid pKa: 3.247681
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -0.38644823
• LogD (pH = 7.4): -1.5907377
• Log P: 1.8459365
• Molar Refractivity: 153.4742 cm^3
• Polarizability: 61.175343 Å^3
• Polar Surface Area: 200.28 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 90-95°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S485005

A metabolite of Simvastatin.

REFERENCES

• Billecke, S., et al.: Drug Metab. Dispos., 28, 1335 (2000)
• Draganov, D., et al.: J. Biol. Chem., 275, 33435 (2000)
• Igel, M., et al.: Eur. J. Clin. Pharmacol., 57, 357 (2000)