(4R)-4-[(1S,2S,5S,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]pentanoic acid

• ChemBase ID: 179405
• 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](CCC(=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](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1
• InChIKey: RUDATBOHQWOJDD-DNMBCGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5S,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]pentanoic acid
• IUPAC Traditional name: (4R)-4-[(1S,2S,5S,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]pentanoic acid
• Synonyms: (3β,5β,7β)-3,7-Dihydroxycholan-24-oic Acid-d5; 3β,7β-Dihydroxy-5β-cholan-24-oic Acid-d5; 3β,7β-Dihydroxy-5β-cholanic Acid-d5; 3β,7β-Dihydroxy-5β-cholanoic Acid-d5; Isoursodeoxycholic Acid-d5; 3β-Ursodeoxycholic Acid-d5

Database IDs

• PubChem SID: 164235315
• PubChem CID: 45040671

CALCULATED PROPERTIES

• Acid pKa: 4.595946
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7592297
• LogD (pH = 7.4): 0.98345095
• Log P: 3.7133055
• Molar Refractivity: 109.2738 cm^3
• Polarizability: 43.768806 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 97-100°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - U850004

Deuterated Ursodeoxcholic Acid (U850005), which is used as an anticholelithogenic.

REFERENCES

• Tint, G.S., et al.: Gastroenterology, 91, 1007 (1986)
• Poupon, R.E, et al.: N. Engl. J. Med., 324, 1548 (1991)