(1S,2R,5R,10S,11S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]-9-oxotetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl acetate

• ChemBase ID: 176081
• Molecular Formular: C29H46O3
• Molecular Mass: 442.67374
• Monoisotopic Mass: 442.34469533
• SMILES: C1[C@H](CC2=CC(=O)[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1[C@@H](CCCC(C)C)C)C)OC(=O)C
• Canonical SMILES: CC(CCC[C@H](C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C(=O)C=C2[C@]1(C)CC[C@H](C2)OC(=O)C)C)C
• InChI: InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(32-20(4)30)16-21(28)17-26(27)31/h17-19,22-25,27H,7-16H2,1-6H3/t19-,22-,23?,24+,25+,27+,28+,29-/m1/s1
• InChIKey: PMBSWZWCNKVWLV-IEOJWWASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10S,11S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]-9-oxotetracyclo[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,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]-9-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• Synonyms: (3β)-3-(Acetyloxy)cholest-5-en-7-one; 3β-Hydroxy-cholest-5-en-7-one Acetate; 7-Ketocholesteryl Acetate; 7-Oxocholest-5-en-3β-yl Acetate; 7-Oxocholesteryl Acetate; NSC 59469; 7-Oxo Cholesterol 3-Acetate

Database IDs

• CAS Number: 809-51-8
• PubChem SID: 164231991
• PubChem CID: 71751394

CALCULATED PROPERTIES

• Acid pKa: 17.204218
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.990509
• LogD (pH = 7.4): 6.990509
• Log P: 6.990509
• Molar Refractivity: 130.412 cm^3
• Polarizability: 51.82931 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - O869985

Intermediate in the preparation of various Cholesterol derivatives and metabolites.

REFERENCES

• Khan, S., et al.: Eur. J. Med. Chem., 43, 2272 (2008)
• Carvalho, J., et al.: J. Med. Chem., 52, 4007 (2008)
• Cui, J., et al.; Steroids, 74, 62 (2008)