methyl (3R)-3-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-bis(acetyloxy)-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]butanoate

• ChemBase ID: 166779
• Molecular Formular: C28H44O6
• Molecular Mass: 476.64536
• Monoisotopic Mass: 476.31378913
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H]([C@@H](C2)OC(=O)C)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CC(=O)OC)C)C)C)OC(=O)C
• Canonical SMILES: COC(=O)C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](OC(=O)C)C[C@H]2[C@]1(C)CC[C@H](C2)OC(=O)C)C
• InChI: InChI=1S/C28H44O6/c1-16(13-25(31)32-6)21-7-8-22-26-23(10-12-28(21,22)5)27(4)11-9-20(33-17(2)29)14-19(27)15-24(26)34-18(3)30/h16,19-24,26H,7-15H2,1-6H3/t16-,19+,20-,21-,22+,23+,24-,26+,27+,28-/m1/s1
• InChIKey: SSSUNRYYXMSDPC-AETVFEKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3R)-3-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-bis(acetyloxy)-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoate
• IUPAC Traditional name: methyl (3R)-3-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-bis(acetyloxy)-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoate
• Synonyms: (3α,5β,7β)-3,7-Bis(acetyloxy)-24-norcholan-23-oic-d5 Acid Methyl Ester; 3α,7β-Di-O-acetyl 24-Nor Ursodeoxycholic Acid-d5 Methyl Ester

Database IDs

• PubChem SID: 162260912
• PubChem CID: 71315877

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.2968817
• LogD (pH = 7.4): 4.2968817
• Log P: 4.2968817
• Molar Refractivity: 127.7449 cm^3
• Polarizability: 51.696754 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D353402

Protected 24-Nor Ursodeoxycholic Acid-d5 (N865302). 24-norUrsodeoxycholic acid is superior to Ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice.

REFERENCES

• Seedorf, U., et al.: J. Biol. Chem., 269, 21277 (1994)
• Stolowich, N., et al.: Biochemistry, 36, 1719 (1997)