(2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-14-[(2R)-5-hydroxypentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 172087
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: C1C(=O)C[C@H]2[C@](C1)(C1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@@H]([C@@H](CCCO)C)CC2)C)C
• Canonical SMILES: OCCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC1[C@H]2[C@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2)C
• InChI: InChI=1S/C24H40O4/c1-14(5-4-10-25)17-6-7-18-22-19(13-21(28)24(17,18)3)23(2)9-8-16(26)11-15(23)12-20(22)27/h14-15,17-22,25,27-28H,4-13H2,1-3H3/t14-,15-,17-,18+,19?,20-,21+,22+,23+,24-/m1/s1
• InChIKey: WKLORKLFLMTHHY-FIGJLYOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-14-[(2R)-5-hydroxypentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: (2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-14-[(2R)-5-hydroxypentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• Synonyms: (5α,7α,12α)-7,12,24-Trihydroxycholan-3-one; 3-Ketopetromyzonol; 3-Keto Petromyzonol

Database IDs

• CAS Number: 359436-56-9
• PubChem SID: 164227997
• PubChem CID: 71669104

CALCULATED PROPERTIES

• Acid pKa: 16.785439
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.573558
• LogD (pH = 7.4): 2.5735583
• Log P: 2.5735583
• Molar Refractivity: 110.0245 cm^3
• Polarizability: 43.94905 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; DMSO
• Apperance: White Crystalline Powder
• Melting Point: double 173-175°C solidifies and melts at 195°C

DETAILS

Toronto Research Chemicals - K200000

Synthetic keto-derivative of Petromyzonol (P293500), a bile salt derivative isolated from the sea lamprey (Petromyzon marinus ) ammocoete (larval form). May be used to study the biochemical characteristics of these and other compounds containing the allo

REFERENCES

• Haslewood, G., et al.: Biochem. J., 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1969)
• Krasowski, M., et al.: Mol. Endocrinol., 19, 1720 (1969)