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

• ChemBase ID: 163758
• Molecular Formular: C27H42O4
• Molecular Mass: 430.61998
• Monoisotopic Mass: 430.30830982
• 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(C)C(=O)O)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC(=O)[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCCC(C(=O)O)C)C)C)C1)C
• InChI: InChI=1S/C27H42O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-22,24,28H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20-,21+,22+,24+,26+,27-/m1/s1
• InChIKey: QOEPZHFZXUROGV-YYRFMTRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-2-methylheptanoic acid
• IUPAC Traditional name: (6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-2-methylheptanoic acid
• Synonyms: (3β)-3-Hydroxy-7-oxocholest-5-en-26-oic Acid; 27-Carboxy-7-keto Cholesterol

Database IDs

• CAS Number: 148988-30-1
• PubChem SID: 162257893
• PubChem CID: 67569451

CALCULATED PROPERTIES

• Acid pKa: 4.828921
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.730675
• LogD (pH = 7.4): 2.95821
• Log P: 5.485109
• Molar Refractivity: 122.9518 cm^3
• Polarizability: 48.50183 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C178525

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)