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

• ChemBase ID: 172054
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: C1[C@@H](CC2=CC(=O)[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1[C@@H](CCCC(C)C)C)C)O
• Canonical SMILES: CC(CCC[C@H](C1CC[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/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21?,22+,23+,25+,26+,27-/m1/s1
• InChIKey: YIKKMWSQVKJCOP-SBMSYAAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-9-one
• IUPAC Traditional name: (1S,2R,5S,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-9-one
• Synonyms: (3β)-3-Hydroxycholest-5-en-7-one; 3β-Hydroxycholest-5-en-7-one; 7-Oxocholesterol; Cholest-5-en-3β-ol-7-one; SC 4722; 7-Keto Cholesterol

Database IDs

• CAS Number: 566-28-9
• PubChem SID: 164227964
• PubChem CID: 50990351

CALCULATED PROPERTIES

• Acid pKa: 17.38833
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.5493836
• LogD (pH = 7.4): 6.5493836
• Log P: 6.5493836
• Molar Refractivity: 121.2605 cm^3
• Polarizability: 48.014973 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - K185050

A metabolite of Cholesterol.

REFERENCES

• Wang, J., et al.: Biochemistry, 43, 1010 (2004)
• Lemaire-Ewing, S., et al.: Cell Biol. Toxicol., 21, 97 (2004)
• Fuda, H., et al.: J. Lipid Res., 48, 1343 ( 2007), Sasaki, H., et al.: Metabolism, 56, 357 (2004)