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Chemical Structure| 85590-00-7 Chemical Structure| 85590-00-7
Chemical Structure| 85590-00-7

10-(Phosphonooxy)decyl methacrylate

CAS No.: 85590-00-7

4.5 *For Research Use Only !

Cat. No.: A269465 Purity: 95%

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Product Citations

Product Citations

Araújo-Neto, Vitaliano Gomes ; Rifane, Tainah Oliveira ; André, Carolina Bosso ; Zattera, Ana Cristina Andrioli ; de Souza Balbinot, Gabriela ; Collares, Fabrício Mezzomo , et al.

Abstract: Objective: To evaluate the effects of experimental primers containing 10-methacryloyloxydecyl dihydrogen phosphate (10-MDP) and/or γ-methacryloxypropyltrimethoxysilane (γ-MPTS) on the adhesion and chemical interaction with zirconia ceramics. Materials & methods: Two ethanol-based experimental primers were prepared: 5 wt% 10-MDP (MDP-E) and 5 wt % 10-MDP + 5 wt% γ-MPTS (MDP-S). A commercial primer (CLE-C, Clearfil Ceramic Primer) was used as control. Three types of zirconia ceramics were used: 3Y-TZP, 4Y-PSZ, and 5Y-PSZ. Experimental and Control primers were applied to zirconia ceramics and the shear bond strength (SBS) to primed zirconia were tested after 24h or after 150 days in water + 12,000 cycles of thermocycling (TC) (n = 8). Primed zirconia surface compositions were analyzed using energy dispersive X-ray spectroscopy (EDX) (n = 3). Surface free energy (SFE) of primed zirconia was determined by contact angle measurement using water or diiodomethane (n = 10). MicroRaman spectroscopy investigated the vibrational peak of 10-MDP bonded to primed zirconia (n = 3). SBS and SFE data were analyzed by three-way or two-way ANOVA, Bonferroni, and post-hoc Tukey test (α = 0.05). Results: CLE-C primer did not differ from the experimental primers at 24 h and after TC. The SBS reduced for all groups after TC. When CLE-C was applied to zirconia ceramics, the highest SFE was obtained for 3Y-TZP one. SFE did not differ among zirconia ceramics when MDP-E primer was used. MDP-E did not differ from other primers or yielded higher SFE, depending on the type of zirconia. EDX indicated similar elemental compositions for the primed zirconia ceramics with CLE-C and MDP-S. Raman spectroscopy revealed chemical interaction only between the primers and 3Y-TZP. Conclusions: In general, CLE-C primer yielded the best SBS results, while MDP-E the SFE ones. Although EDX identified phosphorus chemical element on all primed zirconia surfaces after primer applications, the chemical interaction was observed only between the primers and 3Y-TZP.

Keywords: Silanes ; Ceramics ; Raman spectroscopy ; Dental materials

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Product Details of [ 85590-00-7 ]

CAS No. :85590-00-7
Formula : C14H27O6P
M.W : 322.33
SMILES Code : CC(C(OCCCCCCCCCCOP(O)(O)=O)=O)=C
MDL No. :MFCD19441164
InChI Key :CFKBCVIYTWDYRP-UHFFFAOYSA-N
Pubchem ID :135071

Safety of [ 85590-00-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 85590-00-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 0
Fraction Csp3 0.79
Num. rotatable bonds 14
Num. H-bond acceptors 6.0
Num. H-bond donors 2.0
Molar Refractivity 82.3
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

102.87 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.02
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.9
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.34
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.73
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.56

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.74
Solubility 0.585 mg/ml ; 0.00181 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.72
Solubility 0.00613 mg/ml ; 0.000019 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.04
Solubility 0.296 mg/ml ; 0.000918 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.21 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.57
 

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