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[ CAS No. 3849-21-6 ] {[proInfo.proName]}

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Chemical Structure| 3849-21-6
Chemical Structure| 3849-21-6
Structure of 3849-21-6 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Calabretta, Lindsey O. ; Yang, Jinyi ; Raines, Ronald T. DOI: PubMed ID:

Abstract: The field of cell-penetrating peptides is dominated by the use of oligomers of arginine residues. Octanol-water partitioning in the presence of an anionic lipid is a validated proxy for cell-penetrative efficacy. Here, we add one, two, or three N-Me groups to Ac-Arg-NH2 and examine the effects on octanol-water partitioning. In the absence of an anionic lipid, none of these arginine derivatives can be detected in the octanol layer. In the presence of sodium dodecanoate, however, increasing N-methylation correlates with increasing partitioning into octanol, which is predictive of higher cell-penetrative ability. We then evaluated fully Nα-methylated oligoarginine peptides and observed an increase in their cellular penetration compared with canonical oligoarginine peptides in some contexts. These findings indicate that a simple modification, Nα-methylation, can enhance the performance of cell-penetrating peptides.

Keywords: guanidino group ; octanol-water partitioning ; peptoid ; topological polar surface area

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Product Details of [ 3849-21-6 ]

CAS No. :3849-21-6 MDL No. :MFCD00002112
Formula : C5H6N2O3 Boiling Point : -
Linear Structure Formula :C(CN)CO(OC2H5)NOH InChI Key :-
M.W : 142.11 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 3849-21-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.6
TPSA : 82.68 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : -0.1
Log Po/w (MLOGP) : -1.06
Log Po/w (SILICOS-IT) : -0.19
Consensus Log Po/w : 0.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.35
Solubility : 6.28 mg/ml ; 0.0442 mol/l
Class : Very soluble
Log S (Ali) : -2.66
Solubility : 0.313 mg/ml ; 0.0022 mol/l
Class : Soluble
Log S (SILICOS-IT) : 0.06
Solubility : 163.0 mg/ml ; 1.15 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.21

Safety of [ 3849-21-6 ]

Signal Word:Danger Class:4.1,6.1
Precautionary Statements:P210-P240-P264-P270-P280-P301+P310-P330-P370+P378-P403+P233-P405-P501 UN#:2926
Hazard Statements:H228-H301-H317-H319 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 3849-21-6 ]

* 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.

  • Upstream synthesis route of [ 3849-21-6 ]
  • Downstream synthetic route of [ 3849-21-6 ]

[ 3849-21-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 3849-21-6 ]
  • [ 37842-58-3 ]
Reference： [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 441 - 451
[2] Chemistry - A European Journal, 2015, vol. 21, # 16, p. 6090 - 6099
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