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

• ChemBase ID: 170342
• Molecular Formular: C29H48O3
• Molecular Mass: 444.68962
• Monoisotopic Mass: 444.3603454
• 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)OC(=O)C)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]2OC(=O)C)O)C)C
• InChI: InChI=1S/C29H48O3/c1-18(2)8-7-9-19(3)22-12-13-23-21-10-11-25-27(32-20(4)30)26(31)15-17-29(25,6)24(21)14-16-28(22,23)5/h11,18-19,21-24,26-27,31H,7-10,12-17H2,1-6H3/t19-,21+,22-,23+,24+,26+,27+,28-,29-/m1/s1
• InChIKey: CPAJTVKFJMIGFR-WAJRRKGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,6S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-6-yl acetate
• IUPAC Traditional name: (1S,2R,5S,6S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-6-yl acetate
• Synonyms: (3β,4β)-Cholest-5-ene-3,4-diol 4-Acetate; 4β-Acetoxycholest-5-en-3β-ol; 4β-Hydroxy Cholesterol 4-Acetate

Database IDs

• CAS Number: 2515-18-6
• PubChem SID: 164226252
• PubChem CID: 71748929

CALCULATED PROPERTIES

• Acid pKa: 14.106661
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.6350183
• LogD (pH = 7.4): 6.6350183
• Log P: 6.6350183
• Molar Refractivity: 130.9755 cm^3
• Polarizability: 52.377945 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H917985

Cholesterol (C432501) metabolite. Hydroximinosteroid analog with cytotoxic properties.

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)
• Poza, J. et al.: Bioorgan Med. Chem. 15, 4722