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

• ChemBase ID: 170348
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• 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@@](CCCC(C)C)(O)C)C)O
• Canonical SMILES: CC(CCC[C@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)(O)C)C
• InChI: InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
• InChIKey: MCKLJFJEQRYRQT-MGNSQDQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: 20a-hydroxy cholesterol
• Synonyms: (3β)-Cholest-5-ene-3,20-diol; (20S)-Cholest-5-ene-3β,20-diol; 20S-Cholest-5-ene-3β,20-diol; Cholest-5-ene-3β,20α-diol; 20α-Hydroxy Cholesterol

Database IDs

• CAS Number: 516-72-3
• PubChem SID: 164226258
• PubChem CID: 440711

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.7976813
• LogD (pH = 7.4): 5.797682
• Log P: 5.797682
• Molar Refractivity: 122.2986 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 136-137°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H918000

A metabolite of Cholesterol (C432501). Cholesterol oxidation product having cytotoxicity effects.

REFERENCES

• Higley, N., et al.: Food Chem. Toxicol., 22, 983 (1984)
• Emanuel, H., et al.: J. Food Sci., 56, 843 (1984)
• Kilsdonk, E., et al.: J. Lipid Res., 36, 505 (1984)
• Cantwell, H., et al.: Cell Biol. Toxicol., 14, 401 (1984)