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Chemical Structure| 113479-65-5 Chemical Structure| 113479-65-5

Structure of ACLE HCL
CAS No.: 113479-65-5

Chemical Structure| 113479-65-5

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Product Details of [ 113479-65-5 ]

CAS No. :113479-65-5
Formula : C16H18Cl2N2O4S
M.W : 405.30
SMILES Code : O=C(C(N12)=C(CCl)CS[C@]2([H])[C@H](N)C1=O)OCC3=CC=C(OC)C=C3.[H]Cl
MDL No. :MFCD00191255
InChI Key :LYIIGHOYDRRHAJ-XRZFDKQNSA-N
Pubchem ID :14032024

Safety of [ 113479-65-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H317-H334
Precautionary Statements:P261-P272-P280-P284-P302+P352-P304+P340+P312
Class:6.1
UN#:2811
Packing Group:

Computational Chemistry of [ 113479-65-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 6
Fraction Csp3 0.38
Num. rotatable bonds 6
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 102.01
TPSA ?

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

107.16 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

1.71
Log Po/w (WLOGP)?

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

1.74
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.

1.89
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

1.88
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.44

Water Solubility

Log S (ESOL):?

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

-3.21
Solubility 0.249 mg/ml ; 0.000614 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.

-3.58
Solubility 0.108 mg/ml ; 0.000265 mol/l
Class?

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

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

-3.73
Solubility 0.075 mg/ml ; 0.000185 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

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

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.

-7.56 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

0.0
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

1.0 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)

4.38

Application In Synthesis of [ 113479-65-5 ]

* 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 [ 113479-65-5 ]

[ 113479-65-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 104146-10-3 ]
  • [ 113479-65-5 ]
YieldReaction ConditionsOperation in experiment
456 g With pyridine; phosphorus pentachloride In methanol; dichloromethane at -30 - 5℃; for 4 h; CH2Cl2 (3L), PCl5 (374.4g) were added to 10L of the reaction flask, the temperature was stirred at room temperature down to about 0 ° C, pyridine (200mL) was slowly added dropwise to control the dropping rate,So that the internal temperature should not exceed 5 . The reaction was continued after 1h cooled to -5 , GCLE was added in portions(7Phenylacetamide-3-chloromethyl cephalanacrylate p-methoxybenzyl ester, 584.4g), controlling the internal temperature between -5 to 0 , the reaction was continued for 3h. Rapid cooling to -30 , the beginning slowly dropping methanol (1500mL), continue to -30 for 1h. The temperature was raised to -10 ° C, and 1500 mL of water was added dropwise. The temperature was controlled to -10 to 0 ° C for 1 hour. Finally, 1500mL of water was added once more and the mixture was stirred for 5min. The reaction solution was poured into a beaker with a lower mouth and was allowed to stand for delamination. The organic phase was taken off and a small amount of CH2Cl2 was added to the aqueous phase. The combined organic phases were dried over anhydrous sodium sulfate 1000g) dried,Suction filtration, the filter cake was washed with a small amount of CH2Cl2, the filtrate was added dropwise to isopropyl ether (12L) and stirred overnight. The next day, suction filtration, the filter cake was washed with a small amount of isopropyl ether, pale yellow solid, scraped the material, dried in vacuo overnight to give the product 456g.
References: [1] Patent: CN106317077, 2017, A, . Location in patent: Paragraph 0010; 0011l 0012.
  • 2
  • [ 104146-10-3 ]
  • [ 113479-65-5 ]
References: [1] Tetrahedron Letters, 1987, vol. 28, # 24, p. 2745 - 2746.
 

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