(1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0?,?.0??,??]heptadecane-5,7,8-triol

• ChemBase ID: 112774
• Molecular Formular: C27H48O3
• Molecular Mass: 420.66822
• Monoisotopic Mass: 420.3603454
• SMILES: O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@@H]4CC[C@@H]([C@@]4(C)CC3)[C@H](C)CCCC(C)C)C[C@@H](O)[C@@]2(O)C1)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H]([C@@]2([C@]1(C)CC[C@@H](C2)O)O)O)C)C
• InChI: InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
• InChIKey: YMMFNKXZULYSOQ-RUXQDQFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0?,?.0??,??]heptadecane-5,7,8-triol; (1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,7,8-triol
• IUPAC Traditional name: cholestane-3β-5α,6β-triol
• Synonyms: CHOLESTANE-3β,5α,6β-TRIOL; (3β,5α,6β)-Cholestane-3,5,6-triol; 3β-Hydroxycholestane-5α,6β-diol; 5α,6β-Dihydroxycholestanol; Cholesta-3β,5α,6β-triol; Cholestane-3β,5α,6β-triol; NSC 124751; NSC 18178; 3β,5α,6β-Trihydroxycholestane

Database IDs

• CAS Number: 1253-84-5
• PubChem SID: 162097641
• PubChem CID: 91498

CALCULATED PROPERTIES

• Rotatable Bonds: 5
• Lipinski's Rule of Five: false
• Acid pKa: 13.287488
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.211471
• LogD (pH = 7.4): 5.2114706
• Log P: 5.211471
• Molar Refractivity: 122.6125 cm^3
• Polarizability: 49.40406 Å^3
• Polar Surface Area: 60.69 Å^2

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 226-231°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

MP Biomedicals - 05225755

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - T795100

Cholesterol analog. Useful for treatment of hyperlipemia, arteriosclerosis, diabetes, obesity.

REFERENCES

• Watson, K., et al.: J. Clin. Invest., 93, 2106 (1994)
• Wada, T., et al.: Circ. Res., 84, 166 (1994)
• Engelse, M., et al.: Cardiovasc. Res., 52, 281 (1994)
• Landis, M., et al.: J. Biol. Chem., 277, 4713 (1994)