(3R)-3-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]butanoic acid

• ChemBase ID: 175588
• Molecular Formular: C23H38O5
• Molecular Mass: 394.54482
• Monoisotopic Mass: 394.27192432
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([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]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CC(=O)O)C)C)O)C
• InChI: InChI=1S/C23H38O5/c1-12(8-20(27)28)15-4-5-16-21-17(11-19(26)23(15,16)3)22(2)7-6-14(24)9-13(22)10-18(21)25/h12-19,21,24-26H,4-11H2,1-3H3,(H,27,28)/t12-,13+,14-,15-,16+,17+,18-,19+,21+,22+,23-/m1/s1
• InChIKey: SHUYNJFEXPRUGR-RTCCEZQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-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,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoic acid
• Synonyms: (3α,5β,7α,12α)-3,7,12-Trihydroxy-24-norcholan-23-oic Acid; 3α,7α,12α-Trihydroxy- 23-nor-5β-cholanic Acid; 23-Norcholic Acid; 24-Norcholic Acid; 3α,7α,12α-Trihydroxy-24-nor-5β-cholan-23-oic Acid; Norcholic Acid; Nor Cholic Acid

Database IDs

• CAS Number: 60696-62-0
• PubChem SID: 164231498
• PubChem CID: 158738

CALCULATED PROPERTIES

• Acid pKa: 4.418963
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.92380077
• LogD (pH = 7.4): -0.83539563
• Log P: 2.0379257
• Molar Refractivity: 106.1883 cm^3
• Polarizability: 42.56717 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Tan to Pale Yellow Solid
• Melting Point: 181-184°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N661440

A novel bile acid, an analogue of Cholic acid (C432600).

REFERENCES

• Yamaga, N., et al.: J. Biochem., 116, 1123 (1994)