(2R,3R,4R,5S,6R)-6-{[(4R)-4-[(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]pentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179407
• Molecular Formular: C30H48O10
• Molecular Mass: 568.69612
• Monoisotopic Mass: 568.32474774
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OC(=O)CC[C@H]([C@@H]1[C@@]2([C@H]([C@@H]3[C@H](C[C@@H]4C[C@@H](CC[C@@]4([C@H]3CC2)C)O)O)CC1)C)C
• 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@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)C)C)O)C
• InChI: InChI=1S/C30H48O10/c1-14(4-7-21(33)39-28-25(36)23(34)24(35)26(40-28)27(37)38)17-5-6-18-22-19(9-11-30(17,18)3)29(2)10-8-16(31)12-15(29)13-20(22)32/h14-20,22-26,28,31-32,34-36H,4-13H2,1-3H3,(H,37,38)/t14-,15+,16-,17-,18+,19+,20+,22+,23-,24-,25+,26-,28+,29+,30-/m1/s1
• InChIKey: ZTJBLIAPAIPNJE-COPMGDDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[(4R)-4-[(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]pentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[(4R)-4-[(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]pentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(3α,5β,7β)-3,7-Dhydroxycholan-24-oate-β-D-glucopyranuronic Acid; Ursodeoxycholic Acid Acyl-β-D-glucuronide, >85%

Database IDs

• CAS Number: 208038-28-2
• PubChem SID: 164235317
• PubChem CID: 71752896

CALCULATED PROPERTIES

• Acid pKa: 3.2465818
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.46797886
• LogD (pH = 7.4): -1.6713873
• Log P: 1.765512
• Molar Refractivity: 141.5724 cm^3
• Polarizability: 57.556248 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >120°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - U850010

A metabolite of Ursodeoxycholic acid. Contains products of acyl migration which were not individually quantified.

REFERENCES

• Alme, B., et al.: J. Steroid Biochem., 13, 907 (1980)
• Radominska-Pyrek, A., et al.: J. Clin. Invest., 80, 234 (1980)