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Structure of 50461-74-0

Chemical Structure| 50461-74-0

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Product Details of [ 50461-74-0 ]

CAS No. :50461-74-0
Formula : C7H12O3
M.W : 144.17
SMILES Code : C(C)CC(C(OCC)=O)=O
MDL No. :MFCD06410882
InChI Key :YERWBBMSDMSDKT-UHFFFAOYSA-N
Pubchem ID :123521

Safety of [ 50461-74-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 50461-74-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.71
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 37.25
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.08
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

1.19
Log Po/w (WLOGP)?

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

0.92
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.

0.64
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

1.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.19

Water Solubility

Log S (ESOL):?

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

-1.15
Solubility 10.1 mg/ml ; 0.0702 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.7
Solubility 2.9 mg/ml ; 0.0201 mol/l
Class?

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

Very 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

-1.48
Solubility 4.74 mg/ml ; 0.0329 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

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

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.

-6.33 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

1.0
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)

1.53

Application In Synthesis of [ 50461-74-0 ]

* 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 [ 50461-74-0 ]
  • Downstream synthetic route of [ 50461-74-0 ]

[ 50461-74-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1821-02-9 ]
  • [ 50461-74-0 ]
YieldReaction ConditionsOperation in experiment
71% With ethanol In water; toluene at 80℃; for 3 h; Heating / reflux 0.1 mol of 2,2-(dimethylthio)pentanoic acid (11) (19.4 g) was dissolved in 150 ml of toluene and admixed with 2.0 eq of H2O (3.6 ml) and a spatula-tip of p-toluenesulfonic acid monohydrate. Subsequently, the mixture was heated to boiling point and a nitrogen stream was passed through the solution via a frit. After 3 h under reflux, the reaction mixture was cooled to 80° C. and admixed with 200 ml of ethanol and a further spatula-tip of p-toluenesulfonic acid monohydrate. After a further 3 h under reflux, the mixture was cooled to 20° C., 200 ml of water were added and the mixture was extracted three times with 100 ml each time of diethyl ether. The combined ether phases were subsequently washed to neutrality with a dilute sodium hydrogencarbonate solution and dried over magnesium sulfate. After filtration, all of the solvent was drawn off with a rotary evaporator. The ethyl 2-oxovalerate (12) (10.2 g, yield=71percent) was obtained as a pale yellowish oil.1H NMR of ethyl 2-oxovalerate (12) (500 MHz, CDCl3): δ=0.97 (t, 3J=7.3 Hz, 3H, C5H3), 1.37 (t, 3J=7.3 Hz, 3H, OCH2CH3), 1.67 (sext, 3J=7.3 Hz, 2H, C4H2), 2.81 (t, 3J=7.3 Hz, 2H, C3H3), 4.32 (q, 3J=7.3 Hz, 2H, OCH2CH3)13C NMR of ethyl 2-oxovalerate (12) (125.8 MHz, CDCl3): δ=13.5 (OCH2CH3), 14.0 (C-5), 16.6 (C-4), 41.2 (C-3), 62.3 (OCH2CH3), 161.4 (C-1), 194.7 (C-2)
References: [1] Patent: US2009/76302, 2009, A1, . Location in patent: Page/Page column 7.
  • 2
  • [ 64-17-5 ]
  • [ 1821-02-9 ]
  • [ 50461-74-0 ]
YieldReaction ConditionsOperation in experiment
45% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3.66 h; A solution of 2-oxopentanoic acid (3.00 g, 25.8 mmol), ethanol (1.20 g, 25.8 mmol) andDMAP (0.32 g, 2.6 mmol) in dichloromethane (30 mL) was cooled with an ice bathbefore a solution of DCC (5.86 g, 28.4 mmol) in dichloromethane (15 mL) was addeddropwise during 30 mm. The reaction mixture was stirred for 10 mm at 0°C, then at roomtemperature for 3 h. The precipitate formed during the reaction was filtered on a sintered glass frit and rinsed with dichloromethane (15 mL). The filtrate was concentrated under reduced pressure (40°C) and the residue taken up in diethylether (100 mL). The organic phase was washed with water (3x 30 mL), an aqueous solution of HC1 (10percent, 3x 30 mL), water (30 mL), a saturated aqueous solution of NaHCO3 (3x 30 mL) and water (30 mL). The aqueous phases were re-extracted with diethylether (100 mL). The combined organicphases were dried (Na2SO4) and concentrated under reduced pressure (45°C). Bulb-to- bulb distillation (120°C, 8 mbar) gave 1.80 (45percent) g of a colorless oil.‘H-NMR (500 MHz): ö 4.32 (q, I = 7.2, 2 H), 2.82 (t, I = 7.2, 2 H), 1.67 (hex., I = 7.4, 2 H), 1.37 (t, I = 7.2, 3 H), 0.97 (t, I = 7.5, 3 H).‘3C-NMR (125.8 MHz): ö 194.67 (s), 161.32 (s), 62.35 (t), 41.14 (t), 16.54 (t), 14.03 (q),13.52 (q).
References: [1] Patent: WO2014/187833, 2014, A1, . Location in patent: Page/Page column 24; 25.
[2] Journal of Organic Chemistry, 1988, vol. 53, # 11, p. 2589 - 2593.
  • 3
  • [ 3249-68-1 ]
  • [ 50461-74-0 ]
References: [1] Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7268 - 7273.
  • 4
  • [ 79584-44-4 ]
  • [ 50461-74-0 ]
References: [1] Tetrahedron, 1997, vol. 53, # 49, p. 16767 - 16782.
  • 5
  • [ 26103-77-5 ]
  • [ 50461-74-0 ]
References: [1] Helvetica Chimica Acta, 1950, vol. 33, p. 116,124.
[2] Journal of Organic Chemistry, 1988, vol. 53, # 11, p. 2589 - 2593.
  • 6
  • [ 14273-07-5 ]
  • [ 50461-74-0 ]
References: [1] Recueil des Travaux Chimiques des Pays-Bas, 1961, vol. 80, p. 846 - 848.
  • 7
  • [ 615-83-8 ]
  • [ 50461-74-0 ]
References: [1] Journal of Organic Chemistry, 1979, vol. 44, p. 1835 - 1839.
  • 8
  • [ 927-77-5 ]
  • [ 95-92-1 ]
  • [ 50461-74-0 ]
References: [1] Synthetic Communications, 1981, vol. 11, # 12, p. 943 - 946.
  • 9
  • [ 69461-35-4 ]
  • [ 50461-74-0 ]
References: [1] Journal of Organic Chemistry, 1979, vol. 44, p. 1835 - 1839.
 

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