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

• ChemBase ID: 170169
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@H](C2)O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCCC(C)C)C)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H](O)CC2=CC(=O)CC[C@]12C)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/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24+,25+,26+,27-/m1/s1
• InChIKey: IOIZWEJGGCZDOL-BXLWXSRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9S,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,9S,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (7β)-7-Hydroxycholest-4-en-3-one; 4-7β-Hydroxycholestenone; 7β-Hydroxy-4-cholesten-3-one

Database IDs

• CAS Number: 25876-54-4
• PubChem SID: 164226079
• PubChem CID: 5284280

CALCULATED PROPERTIES

• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false
• Acid pKa: 17.141195
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.37137
• LogD (pH = 7.4): 6.3713703
• Log P: 6.3713703
• Molar Refractivity: 121.1576 cm^3
• Polarizability: 48.014973 Å^3

DETAILS

Toronto Research Chemicals - H825125

A metabolite of Cholesterol.

REFERENCES

• Connor, W., et al.: J, Clin. Invest., 48, 1363 (1969)
• Nestel, P., et al.: Metabolism, 24, 189 (1969)
• Ellegard, L., et al.: Eur. J. Clin. Nutr., 45, 451 (1969)
• Pedersen, A., et al.: J. Lipid Res., 41, 1901 (1969)