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

• ChemBase ID: 170350
• 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)CO)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(C)C)C)C)O
• Canonical SMILES: OC[C@]12CC[C@@H](CC1=CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCCC(C)C)C)C)O
• InChI: InChI=1S/C27H46O2/c1-18(2)6-5-7-19(3)23-10-11-24-22-9-8-20-16-21(29)12-15-27(20,17-28)25(22)13-14-26(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t19-,21+,22+,23-,24+,25+,26-,27-/m1/s1
• InChIKey: YRWIUNJQYGATHV-FTLVODPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,10S,11S,14R,15R)-2-(hydroxymethyl)-15-methyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: (1S,2S,5S,10S,11S,14R,15R)-2-(hydroxymethyl)-15-methyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: (3β)-Cholest-5-ene-3,19-diol; Cholest-5-ene-3β,19-diol; 3β,19-Dihydroxycholest-5-ene; 19-Hydroxy Cholesterol

Database IDs

• CAS Number: 561-63-7
• PubChem SID: 164226260
• PubChem CID: 6453303

CALCULATED PROPERTIES

• Acid pKa: 18.204174
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.8321176
• LogD (pH = 7.4): 5.832118
• Log P: 5.832118
• Molar Refractivity: 122.3912 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H918005

A metabolite of Cholesterol. 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)