(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,15R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 179403
• Molecular Formular: C24H40O5
• Molecular Mass: 408.5714
• Monoisotopic Mass: 408.28757438
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H]([C@H](C2)O)[C@H]2[C@](C(C1)O)(C(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(O)[C@]2([C@H]1CCC2[C@@H](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16?,17+,18+,19+,20?,22+,23+,24-/m1/s1
• InChIKey: BHQCQFFYRZLCQQ-QPKJLDHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,15R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,15R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• Synonyms: (3α,5β,7β,12α)-3,7,12-Trihydroxycholan-24-oic Acid; 3α,7β,12α-Trihydroxy-5β-cholanic Acid; 3α,7β,12α-Trihydroxy-5β-cholan-24-oic Acid; 3α,7β,12α-Trihydroxy-5β-cholanoic Acid; 3α,7β,12α-Trihydroxycholanic Acid; 7-Epicholic Acid; 7β-Hydroxyisocholic Acid; Ursocholic Acid

Database IDs

• CAS Number: 2955-27-3
• PubChem SID: 164235313
• PubChem CID: 71752895

CALCULATED PROPERTIES

• Acid pKa: 4.4750123
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4196734
• LogD (pH = 7.4): -0.346591
• Log P: 2.4824944
• Molar Refractivity: 110.7893 cm^3
• Polarizability: 44.403893 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - U849900

Ursodeoxycholic acid (U850000) impurity.

REFERENCES

• Ward, A., et al.: Drugs, 1984, 27, 95 (1984)
• Sama, C., et al.: Clin. Drug Invest., 13, 192 (1984)
• Nobilis, M., et al.: J. Pharm. Biomed. Anal., 24, 937 (1984)