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

• ChemBase ID: 170337
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• 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(C)C(=O)O)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[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/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18?,20+,21+,22-,23+,24+,26+,27-/m1/s1
• InChIKey: WVXOMPRLWLXFAP-AMQKJUDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[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-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-2-methylheptanoic acid
• Synonyms: 3β-Hydroxycholest-5-en-26-oic Acid; Cholesterol-26-carboxylic Acid; β-Hydroxycholest-5-en-26-oic Acid; 3β-Hydroxy-5-cholestenoic Acid

Database IDs

• CAS Number: 6561-58-6
• PubChem SID: 164226247
• PubChem CID: 165511

CALCULATED PROPERTIES

• Acid pKa: 4.828921
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.2941804
• LogD (pH = 7.4): 3.5217154
• Log P: 6.0486145
• Molar Refractivity: 122.3078 cm^3
• Polarizability: 48.432766 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H917500

A metabolite of Cholesterol. Elimination of Cholesterol in human endothelial cells.

REFERENCES

• Prasad, V., et al.: J. Steroid Biochem., 21, 733 (1984)
• Duane, W., et al.: J. Clin. Invest., 92, 911 (1984)
• Lehmann, J., et al.: J. Biol. Chem., 272, 3137 (1984)
• Setchell, K., et al.: J. Clin. Invest., 102, 1690 (1984)
• Song, C., et al.: Endocrinology,