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

• ChemBase ID: 170678
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1[C@@H](CC2=CC(=O)[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(CO)C)C)C)O
• Canonical SMILES: OCC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C(=O)C=C2[C@]1(C)CC[C@@H](C2)O)C)C
• InChI: InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-23,25,28-29H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
• InChIKey: LFNAJBFFWWMSEW-ANDJGGKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-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-9-one
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-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-9-one
• Synonyms: (3β)-3,26-Dihydroxycholest-5-en-7-one; 27-Hydroxy-7-keto Cholesterol

Database IDs

• CAS Number: 148988-28-7
• PubChem SID: 164226588
• PubChem CID: 57307033

CALCULATED PROPERTIES

• Acid pKa: 17.38833
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.1906586
• LogD (pH = 7.4): 5.1906586
• Log P: 5.1906586
• Molar Refractivity: 123.1122 cm^3
• Polarizability: 48.616493 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H943625

A cytostatic sterol for treatment of cancer and other conditions associated with rapidly growing cells.

REFERENCES

• Shoda, J., et al.: Steroids, 58, 119 (1993)
• Axelson, M., et al.: J. Biol. Chem., 271, 12724 (1993)