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

• ChemBase ID: 175730
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H]([C@H](C2)O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CC(=O)OC)C)C)C)O
• 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](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C
• InChI: InChI=1S/C24H40O4/c1-14(11-21(27)28-4)17-5-6-18-22-19(8-10-24(17,18)3)23(2)9-7-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,5-13H2,1-4H3/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
• InChIKey: WTAVEKBGEXLMTO-UZVSRGJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3R)-3-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-5,9-dihydroxy-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,9S,10R,11S,14R,15R)-5,9-dihydroxy-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-Dihydroxy-24-norcholan-23-oic-d5 Acid Methyl Ester; 24-Nor Ursodeoxycholic Acid-d5 Methyl Ester

Database IDs

• PubChem SID: 164231640
• PubChem CID: 71751256

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.4146307
• LogD (pH = 7.4): 3.414631
• Log P: 3.414631
• Molar Refractivity: 109.4419 cm^3
• Polarizability: 44.02125 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-whtie Solid

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - N865307

Labelled Ursodeoxycholic Acid (U850000) derivative. 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 (1994)