(3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]butanoic acid

• ChemBase ID: 175727
• Molecular Formular: C23H38O4
• Molecular Mass: 378.54542
• Monoisotopic Mass: 378.2770097
• 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)O)C)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CC(=O)O)C)C)O)C
• InChI: InChI=1S/C23H38O4/c1-13(10-20(26)27)16-4-5-17-21-18(7-9-23(16,17)3)22(2)8-6-15(24)11-14(22)12-19(21)25/h13-19,21,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14+,15-,16-,17+,18+,19+,21+,22+,23-/m1/s1
• InChIKey: QYYDXDSPYPOWRO-JHMCBHKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoic acid
• IUPAC Traditional name: (3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoic acid
• Synonyms: (3α,5β,7β)-3,7-Dihydroxy-24-norcholan-23-oic Acid; 3α,7β-Dihydroxy-24-nor-5β-cholan-23-oic Acid; Norursodeoxycholic Acid; 24-Nor Ursodeoxycholic Acid

Database IDs

• CAS Number: 99697-24-2
• PubChem SID: 164231637
• PubChem CID: 192254

CALCULATED PROPERTIES

• Acid pKa: 4.5264406
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.2525156
• LogD (pH = 7.4): 0.48125497
• Log P: 3.2687368
• Molar Refractivity: 104.6728 cm^3
• Polarizability: 41.929417 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N865300

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)