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1175-06-0 | Cholestan-6-one, 3-hydroxy-, (3β,5α)-
CAS No: 1175-06-0 Catalog No: AG000EDK MDL No:
Product Description
Catalog Number:
AG000EDK
Chemical Name:
Cholestan-6-one, 3-hydroxy-, (3β,5α)-
CAS Number:
1175-06-0
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
IUPAC Name:
(3S,5S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
InChI:
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,26-,27-/m1/s1
InChI Key:
JQMQKOQOLPGBBE-ZNCJEFCDSA-N
SMILES:
CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)[C@@H]2[C@]1(C)CC[C@@H](C2)O)C)C
EC Number:
214-640-5
UNII:
2V12D4A742
Properties
Complexity:
612
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
9
Defined Bond Stereocenter Count:
0
Exact Mass:
402.35g/mol
Formal Charge:
0
Heavy Atom Count:
29
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
402.663g/mol
Monoisotopic Mass:
402.35g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.7
Literature
| Title | Journal |
|---|---|
| Probing amphotericin B single channel activity by membrane dipole modifiers. | PloS one 20120101 |
| The local electric field within phospholipid membranes modulates the charge transfer reactions in reaction centres. | Biochimica et biophysica acta 20090801 |
| Effect of agents modifying the membrane dipole potential on properties of syringomycin E channels. | Langmuir : the ACS journal of surfaces and colloids 20070619 |
| Comparison of excitation and emission ratiometric fluorescence methods for quantifying the membrane dipole potential. | Biochimica et biophysica acta 20070101 |
| Effect of cholesterol on the interaction of the HIV GP41 fusion peptide with model membranes. Importance of the membrane dipole potential. | Biochemistry 20061226 |
| Effect of the mitochondrial transition pore inhibitor, S-15176, on rat liver mitochondria: ATP synthase modulation and mitochondrial uncoupling induction. | Biochemical pharmacology 20060928 |
| Phlorizin- and 6-ketocholestanol-mediated antagonistic modulation of alamethicin activity in phospholipid planar membranes. | Langmuir : the ACS journal of surfaces and colloids 20060926 |
| Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Its dependence on membrane fluidity. | Mitochondrion 20050801 |
| Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes. | Biochimica et biophysica acta 20050630 |
| Interaction of phloretin and 6-ketocholestanol with DPPC-liposomes as phospholipid model membranes. | International journal of pharmaceutics 20050427 |
| Influence of 6-ketocholestanol on skin permeation of 5-aminolevulinic acid and evaluation of chemical stability. | Journal of pharmaceutical sciences 20041101 |
| Phloretin and 6-ketocholestanol: membrane interactions studied by a phospholipid/polydiacetylene colorimetric assay and differential scanning calorimetry. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20040301 |
| Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes. | Biophysical journal 20031201 |
| Influence of molecular dipoles on human skin permeability: Use of 6-ketocholestanol to enhance the transdermal delivery of bacitracin. | Journal of pharmaceutical sciences 20030501 |
| Influence of phloretin and 6-ketocholestanol on the skin permeation of sodium-fluorescein. | Journal of controlled release : official journal of the Controlled Release Society 20030429 |
| Influence of lipophilic counter-ions in combination with phloretin and 6-ketocholestanol on the skin permeation of 5-aminolevulinic acid. | International journal of pharmaceutics 20030414 |
| Pore formation by 6-ketocholestanol in phospholipid monolayers and its interpretation by a general nucleation-and-growth model accounting for the sigmoidal shape of voltage-clamp curves of ion channels. | Journal of the American Chemical Society 20030402 |
| Effects of the membrane dipole potential on the interaction of saquinavir with phospholipid membranes and plasma membrane receptors of Caco-2 cells. | The Journal of biological chemistry 20011019 |
| Effects of oxygenated sterol on phospholipid bilayer properties: a molecular dynamics simulation. | Chemistry and physics of lipids 20010701 |
| Influence of phloretin and 6-ketocholestanol on the permeation of progesterone through porcine skin. | International journal of pharmaceutics 20010417 |
| Effect of phloretin on ionophore mediated electroneutral transmembrane translocations of H(+), K(+) and Na(+) in phospholipid vesicles. | Biochimica et biophysica acta 20010209 |
| Control of a redox reaction on lipid bilayer surfaces by membrane dipole potential. | Biophysical journal 20010101 |
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