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Chemical Structure| 4132-28-9 Chemical Structure| 4132-28-9

Structure of 4132-28-9

Chemical Structure| 4132-28-9

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Product Details of [ 4132-28-9 ]

CAS No. :4132-28-9
Formula : C34H36O6
M.W : 540.65
SMILES Code : OC1[C@H](OCC2=CC=CC=C2)[C@@H](OCC3=CC=CC=C3)[C@H](OCC4=CC=CC=C4)[C@@H](COCC5=CC=CC=C5)O1
MDL No. :MFCD00066004
InChI Key :OGOMAWHSXRDAKZ-BKJHVTENSA-N
Pubchem ID :10940502

Safety of [ 4132-28-9 ]

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

Computational Chemistry of [ 4132-28-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 40
Num. arom. heavy atoms 24
Fraction Csp3 0.29
Num. rotatable bonds 13
Num. H-bond acceptors 6.0
Num. H-bond donors 1.0
Molar Refractivity 152.6
TPSA ?

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

66.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

4.61
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

4.98
Log Po/w (WLOGP)?

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

5.07
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.

2.86
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

5.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.63

Water Solubility

Log S (ESOL):?

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

-5.92
Solubility 0.000657 mg/ml ; 0.00000122 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-6.11
Solubility 0.000417 mg/ml ; 0.000000771 mol/l
Class?

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

Poorly 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

-10.11
Solubility 0.0000000422 mg/ml ; 0.0000000001 mol/l
Class?

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

Insoluble

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

Yes
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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

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

-6.06 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

1.0
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.

0.55

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

0.0 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<3.0
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)

5.59

Application In Synthesis of [ 4132-28-9 ]

* 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 [ 4132-28-9 ]

[ 4132-28-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 16001-93-7 ]
  • [ 4132-28-9 ]
  • [ 4291-69-4 ]
  • ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 2
  • [ 16001-93-7 ]
  • [ 4132-28-9 ]
  • ((1E,3Z)-(5S,6R)-3,5,7-Tris-benzyloxy-6-hydroxy-hepta-1,3-dienyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 3
  • [ 4132-28-9 ]
  • [ 122194-07-4 ]
  • [ 148171-71-5 ]
YieldReaction ConditionsOperation in experiment
With 4,5-dichloroimidazole; In dichloromethane; at 20℃; for 1.75h; A mixture of 2, 3,4, 6-tetra-D-benzyl-D-mannose (Koto et al., 1976) (940 mg, 1.74 mmol), dimethoxy-N, N-diisopropylphosphoromidate (437 mg, 2.27 mmol) and 4,5-dichloroimidazole (355 mg, 2.61 mmol) in dry dichloromethane (25 mL), under nitrogen, was stirred at room temperature for 105 min. The mixture was poured into water (100 mL) and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate and the solvent was removed. The residue consisting mainly of phosphite 10 was used without further purification.
  • 4
  • [ 4132-28-9 ]
  • [ 122194-07-4 ]
  • 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl dimethyl phosphite [ No CAS ]
YieldReaction ConditionsOperation in experiment
1H-Tetrazole (0.25 g, 3.6 mmol) was addedto a solution of the reducing sugar S5 (1.6g, 3.0 mmol) and i-Pr2NP(OMe)2(0.55 mL, 2.4 mmol) in dry CH2Cl2 (6.0 mL) at 0 C. Themixture was stirred for 5 min and warmed to rt. After being stirred for 45 min,the reaction was quenched with a saturated NaHCO3 aqueous solution(12 mL). The mixture was extracted with CH2Cl2 (100 mL)and the organic layer was washed with saturated NaHCO3 aqueoussolutions (3 × 100 mL). The aqueous layer was then back-extracted with CH2Cl2(100 mL). The combined organic layers were dried over Na2SO4,filtered and concentrated under reduced pressure. The residue was dissolved in freshlydistilled THF (15 mL) and a solution of BH3?THF (0.99 M, 9.0 mL, 8.9mmol) was added to the solution at 0 C. The reaction mixture was stirred for 5min and warmed to rt. After being stirred for 4.5 h, the mixture was concentratedunder reduced pressure. The residue was then dissolved in CHCl3 (100mL) and successively washed with saturated NaHCO3 aqueous solutions(2 × 100 mL) and a brine (100 mL). The aqueous layer was back-extracted withCHCl3 (100 mL). The combined organic layers were dried over Na2SO4,filterd and concentrated under reduced pressure. Purification of the residue bysilica gel column chromatography [hexane-AcOEt (7:1, v/v)] gave8 (1.6 g, 2.4 mmol, quant, a:b = 90:10) as a colorless syrup. The 1Hand 31P NMR spectra were in good agrrement with the reported data.1
 

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