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[ CAS No. 158171-14-3 ] {[proInfo.proName]}

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Chemical Structure| 158171-14-3
Chemical Structure| 158171-14-3
Structure of 158171-14-3 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Abeywardana, Maheeshi Yapa ; Whedon, Samuel D ; Lee, Kwangwoon , et al. DOI: PubMed ID:

Abstract: Sirtuin 2 (Sirt2) is a member of the family of NAD-dependent lysine deacylases and plays important roles in regulation of the and gene expression. As a nucleocytoplasmic deacetylase, Sirt2 has been shown to target both histone and non-histone acetylated protein substrates. The central catalytic domain of Sirt2 is flanked by flexible N- and C-termini, which vary in length and composition with alternative splicing. These termini are further subject to posttranslational modifications (PTMs) including phosphorylation. Here we investigate the function of the N- and C-termini on deacetylation of nuclear substrates by Sirt2. Remarkably, we find that the C-terminus autoinhibits deacetylation, while the N-terminus enhances deacetylation of proteins and , but not nucleosomes—a chromatin model substrate. Using protein semisynthesis we characterize the effect of cell cycle-linked N-terminal phosphorylation at two major phosphorylation sites (Ser23/Ser25) and find that these further enhance protein/peptide deacetylation, with no effect on nucleosome deacetylation. Additionally, we find that VRK1, an established binding partner of both Sirt2 and nucleosomes, can stimulate deacetylation of nucleosomes by Sirt2, likely through an electrostatic mechanism. Taken together, these findings reveal multiple mechanisms regulating the activity of Sirt2, which allow for a broad range of activities across its multiple biological roles.

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Product Details of [ 158171-14-3 ]

CAS No. :158171-14-3 MDL No. :MFCD00797869
Formula : C25H24NO8P Boiling Point : -
Linear Structure Formula :- InChI Key :ZBPUWGDUVAAWJY-QHCPKHFHSA-N
M.W : 497.43 Pubchem ID :11005563
Synonyms :

Calculated chemistry of [ 158171-14-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 35
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.2
Num. rotatable bonds : 12
Num. H-bond acceptors : 8.0
Num. H-bond donors : 3.0
Molar Refractivity : 126.46
TPSA : 141.2 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.15
Log Po/w (XLOGP3) : 2.94
Log Po/w (WLOGP) : 4.16
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 3.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.36
Solubility : 0.0215 mg/ml ; 0.0000432 mol/l
Class : Moderately soluble
Log S (Ali) : -5.57
Solubility : 0.00135 mg/ml ; 0.00000271 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.6
Solubility : 0.000125 mg/ml ; 0.000000252 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.83

Safety of [ 158171-14-3 ]

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

Application In Synthesis of [ 158171-14-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 158171-14-3 ]

[ 158171-14-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 158171-14-3 ]
  • [ 146987-10-2 ]
  • C49H71N11O13PPolS [ No CAS ]
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