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

• ChemBase ID: 164734
• Molecular Formular: C24H40O5
• Molecular Mass: 408.5714
• Monoisotopic Mass: 408.28757438
• SMILES: C1[C@@H](C[C@@H]2[C@](C1)(C1C([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([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](C1C2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[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-YZMSNRQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(2S,5S,7S,9R,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]pentanoic acid
• IUPAC Traditional name: (4R)-4-[(2S,5S,7S,9R,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]pentanoic acid
• Synonyms: (3β,5β,7α,12α)-3,7,12-Trihydroxy-cholan-24-oic Acid; 3-Epicholic Acid; 3β,7α,12α-Trihydroxy-5β-cholanoic Acid; 3β-Cholic Acid

Database IDs

• CAS Number: 3338-16-7
• PubChem SID: 162258869
• PubChem CID: 71314856

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 - C432605

Possible Progesterone metabolite.

REFERENCES

• Meng, L., et al.: J. Hepatol., 27, 346 (1997)
• Ho, C., et al.: Biochem., 45, 5695 (1997)