(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 167794
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCCC(C)C)C)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)CC2=CC(=O)CC[C@]12C)C)C
• InChI: InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h13,16-17,20-25,29-30H,6-12,14-15H2,1-5H3/t17-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: UQPYXHJTHPHOMM-NIBOIBLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 4-cholesten-7α,12α-diol-3-one
• Synonyms: (7α,12α)-7,12-Dihydroxycholest-4-en-3-one; Cholest-4-ene-7α,12α-diol-3-one; 7α,12α-Dihydroxycholest-4-en-3-one

Database IDs

• CAS Number: 1254-03-1
• PubChem SID: 162261927
• PubChem CID: 3081958

CALCULATED PROPERTIES

• Acid pKa: 17.137674
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.1405587
• LogD (pH = 7.4): 5.140559
• Log P: 5.140559
• Molar Refractivity: 122.6731 cm^3
• Polarizability: 48.616493 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ch;loroform
• Apperance: Light Beige Solid
• Melting Point: 215-218°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D452450

A metabolite of Hydroxycholesterol and Hydroxysitosterol.

REFERENCES

• Setchell, K., et al.: J. Clin. Invest., 102, 1690 (1998)
• Song, C., et al.: Endocrinology, 141, 4180 (1998)
• Bjorkhem, I., et al.: J. Biol. Chem., 276, 37004 (1998)
• Edwards, P., et al.: J. Lipid Res., 43, 2 (1998)