(1S,2R,5S,6S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5,6-diol

• ChemBase ID: 170338
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• SMILES: C1[C@@H]([C@H](C2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(C)C)C)C)O)O
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H]([C@H]2O)O)C)C
• InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25+,26-,27-/m1/s1
• InChIKey: CZDKQKOAHAICSF-GFYXKKFXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,6S,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]heptadec-7-ene-5,6-diol
• IUPAC Traditional name: (1S,2R,5S,6S,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]heptadec-7-ene-5,6-diol
• Synonyms: (3β,4α)-Cholest-5-ene-3,4-diol; Cholest-5-ene-3β,4α-diol; 4α-Hydroxy Cholesterol

Database IDs

• CAS Number: 34310-86-6
• PubChem SID: 164226248
• PubChem CID: 12955779

CALCULATED PROPERTIES

• Acid pKa: 13.5001745
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.193893
• LogD (pH = 7.4): 6.1938925
• Log P: 6.193893
• Molar Refractivity: 121.824 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Brownish Orange Solid
• Melting Point: >177°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H917975

A metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.

REFERENCES

• Breuer, O., et al.: J. Lipid Res., 36, 2275 (1995)
• Pikuleva, I., et al.: J. Biol. Chem., 273, 18153 (1995)
• Chawla, A., et al.: Science, 294, 1866 (1995)
• Bodin, K., et al.: J. Biol. Chem., 276, 38685 (1995)