(1S,2R,5R,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl acetate

• ChemBase ID: 159304
• Molecular Formular: C29H48O3
• Molecular Mass: 444.68962
• Monoisotopic Mass: 444.3603454
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@H](C)CCCC(CO)C)C)OC(=O)C
• Canonical SMILES: OCC(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](C2)OC(=O)C)C)C
• InChI: InChI=1S/C29H48O3/c1-19(18-30)7-6-8-20(2)25-11-12-26-24-10-9-22-17-23(32-21(3)31)13-15-28(22,4)27(24)14-16-29(25,26)5/h9,19-20,23-27,30H,6-8,10-18H2,1-5H3/t19?,20-,23-,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: JDAZPBATUQHQGW-ZDOQTMCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• IUPAC Traditional name: (1S,2R,5R,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• Synonyms: Cholest-5-ene-3β,26-diol 3-acetate; (3β)-Cholest-5-ene-3,26-diol 3-Acetate; 3-O-Acetyl-26-hydroxy Cholesterol

Database IDs

• CAS Number: 50681-37-3
• PubChem SID: 162253439
• PubChem CID: 71312913

CALCULATED PROPERTIES

• Acid pKa: 17.418324
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.1952896
• LogD (pH = 7.4): 6.1952896
• Log P: 6.1952896
• Molar Refractivity: 131.6197 cm^3
• Polarizability: 52.377945 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A178850

Intermediate in the production of cholesterol metabolites.

REFERENCES

• Shoda, J., et al.: Steroids, 58, 119 (1993)