97%ee)| A136002|Formula:C23H25NO4|Molecular Weight:379.448950000+ products instock " />

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[ CAS No. 288617-73-2 ] {[proInfo.proName]}

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Chemical Structure| 288617-73-2
Chemical Structure| 288617-73-2
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Christopher J.?Edelmaier ; ?Stephen J.?Klawa ; ?S. Mahsa?Mofidi , et al. DOI:

Abstract: Septins are a class of cytoskeletal proteins that preferentially bind to domains of micron-scale curvature on the cell membrane. Studies have shown that amphipathic helix (AH) domains in septin oligomers are essential for septin curvature sensing. Yet, the underlying mechanochemical interactions that modulate this curvature sensing remain ambiguous. Here we use all-atom molecular dynamics alongside a metadynamics enhanced sampling approach to bridge the gap between time and length scales required to optimize and validate experimental design of amphipathic helices. Simulations revealed that the local charge on the termini of an 18-amino-acid AH peptide impacts its helical content and positioning within lipid membranes. These computational observations are confirmed with experiments measuring the binding of synthetic AH constructs with variable helical content and charged termini to lipid vesicles. Taken together, these results identify the helical content of amphipathic helices as a regulator of septin binding affinity to lipid membranes. Additionally, we examined an extended AH sequence including 8 amino acids upstream and downstream of the minimal 18-amino-acid-long AH domain to more closely mimic the native protein in simulations and experiments. Simulations and experiments show that the extended peptide sequence adopts a strong alpha-helical conformation when free in solution, giving rise to a higher affinity to lipid membranes than that of the shorter AH sequence. Together, these results provide insight into how the native septin proteins interact with membranes, and establish general design principles that can guide the interaction of future synthetic materials with lipid membranes in a programmable manner.

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Product Details of [ 288617-73-2 ]

CAS No. :288617-73-2 MDL No. :MFCD09879888
Formula : C23H25NO4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 379.45 Pubchem ID :-
Synonyms :
Chemical Name :(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhept-6-enoic acid

Calculated chemistry of [ 288617-73-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.3
Num. rotatable bonds : 10
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 108.77
TPSA : 75.63 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.23
Log Po/w (XLOGP3) : 4.7
Log Po/w (WLOGP) : 4.72
Log Po/w (MLOGP) : 3.36
Log Po/w (SILICOS-IT) : 4.37
Consensus Log Po/w : 4.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.81
Solubility : 0.00587 mg/ml ; 0.0000155 mol/l
Class : Moderately soluble
Log S (Ali) : -6.02
Solubility : 0.000365 mg/ml ; 0.000000962 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.51
Solubility : 0.000117 mg/ml ; 0.000000309 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.02

Safety of [ 288617-73-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:
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