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Chemical Structure| 1633-83-6 Chemical Structure| 1633-83-6

Structure of 1633-83-6

Chemical Structure| 1633-83-6

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Product Details of [ 1633-83-6 ]

CAS No. :1633-83-6
Formula : C4H8O3S
M.W : 136.17
SMILES Code : O=S1(CCCCO1)=O
MDL No. :MFCD00006584
InChI Key :MHYFEEDKONKGEB-UHFFFAOYSA-N
Pubchem ID :15411

Safety of [ 1633-83-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H351
Precautionary Statements:P201-P202-P264-P270-P281-P301+P312-P308+P313-P330-P403-P501

Computational Chemistry of [ 1633-83-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 29.28
TPSA ?

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

51.75 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.09
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

0.14
Log Po/w (WLOGP)?

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

1.21
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.

-0.08
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

0.73
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.62

Water Solubility

Log S (ESOL):?

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

-0.77
Solubility 23.0 mg/ml ; 0.169 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.

-0.78
Solubility 22.4 mg/ml ; 0.165 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

-0.62
Solubility 32.4 mg/ml ; 0.238 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.

-7.03 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

2.0
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)

2.88

Application In Synthesis of [ 1633-83-6 ]

* 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.

  • Downstream synthetic route of [ 1633-83-6 ]

[ 1633-83-6 ] Synthesis Path-Downstream   1~4

  • 2
  • [ 1633-83-6 ]
  • [ 53597-69-6 ]
  • [ 1430837-91-4 ]
YieldReaction ConditionsOperation in experiment
86.8% at 25.0℃; for 20.0h;Inert atmosphere; Schlenk technique; 0.300 g (1.9 mmol) of PTA were mixed with 780 μL (7.6 mmol, 4 eq) of 1,4-butanesultone for 20 h without any solvent. 5 mL of ether were then added and the white solid product was separated by filtration and washed with ether (0.483 g, 1.65 mmol, 86.8%). Solubility in water (25 C): 504 mg/mL. Data for 2 were as follows: 1H NMR (300 MHz, D2O, 25 C): δ 1.63 (m, 2H, CH2CH2SO3-), δ 1.80 (m, 2H, CH2CH2SO3-), δ 2.82 (m, 4H, CH2CH2CH2N+), δ 3.80 (m, 4H, PCH2N), δ 4.22 (s, 1H, PCH2N+), δ 4.23 (s, 1H, PCH2N+), δ 4.38 (d, 2JHH = 14 Hz, 1H, NCH2N), δ 4.52 (d, 2JHH = 14 Hz, 1H, NCH2N), δ 4.72 (d, 2JHH = 11 Hz, 2H, NCH2N+), δ 4.90 (d, 2JHH = 11 Hz, 2H, NCH2N+). 13C{1H}NMR (75.43 MHz, D2O, 25 C): δ 18.1 (s CH2SO3-), δ 21.2 (s, CH2CH2CH2SO3-), δ 30.1 (s, CH2CH2CH2N+), δ 45.2 (d, 1JPC = 21.4 Hz, PCH2N), δ 50.4 (s, CH2CH2CH2N+), δ 52.9 (d, 1JPC = 34 Hz, PCH2N+), δ 62.2 (s, CH2CH2N+), δ 69.4 (s, NCH2N), δ 78.8 (s, NCH2N+). 31P{1H} NMR (121.5 MHz, D2O, 25 C): δ -82.86 ppm (s). Anal. Calc. for C10H20N3O3PS (293): C, 40.94; H, 6.88; N, 14.33; S, 10.91. Found: C, 41.03; H, 6.97; N, 14.25; S, 10.82%. Electrospray MS (in H2O): observed m/z (M+H+) 294, (M+Na+) 316, calcd 294 for C10H21N3O3PS (MH+).
75% In acetone; at 60.0℃; for 24.0h;Inert atmosphere; An oven-dried 250 mL three-necked round-bottomed flask equipped with an additional funnel, a thermo-pocket, and a magnetic stir bar was evacuated and flushed with N2 three times. To this flask were added PTA (1.0 g, 1.0 equiv) and acetone (40 mL) under N2 atmosphere. The resulting mixture was stirred for 15 min at r.t. to obtain an almost clear solution. Next, 1,4-butanesultone (1.95 mL, 3.0 equiv) was added dropwise under N2 atmosphere. The reaction mixture was heated for 24 h at 60 C while stirring with a cooling condenser assembly. The mixture was cooled to r.t. and the solvent removed using cannula. The solid product was washed with acetone (3 10 mL) furnishing 1.4 g (75%) of PTABS as a white solid; mp 252-254 C (Lit.34 mp 252-255 C). IR (ATR): 3423, 3019, 2959, 1675, 1471, 1266, 1171, 1128, 1036, 991, 943, 922, 784, 652, 600 cm-1. 1H NMR (500 MHz, D2O): = 4.93 (d, J = 11.7 Hz, 2 H), 4.75 (d, J = 11.7 Hz, 2 H), 4.55 (d, J = 13.7 Hz, 1H), 4.39 (d, J = 13.7 Hz, 1H), 4.28 (d, J = 5.7 Hz, 2 H), 3.91 (t, J = 13.9 Hz, 2 H), 3.80 (dd, J = 14.9, 8.9 Hz, 2 H), 2.91 (dd, J = 17.4, 10.3 Hz, 4 H), 1.86 (dt, J = 16.0, 7.9 Hz, 2 H), 1.72 (dt, J = 14.7, 7.4 Hz, 2 H). 13C NMR{1H} (126 MHz, D2O): = 79.0, 69.5, 62.3, 53.2, 52.9, 49.9, 45.8, 45.7 (d, J = 20.9 Hz), 21.3, 18.2. 31P NMR (162 MHz, D2O): = -84.51. Anal. Calcd for C10H22N3O4PS (PTABS*H2O): C, 38.58; H, 7.12; N, 13.50; S, 10.30. Found: C, 38.87; H, 6.86; N, 13.52; S, 9.96.
  • 3
  • [ 1633-83-6 ]
  • [ 21252-69-7 ]
  • C15H29N2O3S(1+)*HO4S(1-) [ No CAS ]
  • 4
  • [ 1633-83-6 ]
  • [ 83-73-8 ]
  • C13H13I2NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% at 140℃; General procedure: Compounds1a-c, 3a-j,and5a,b (10 mmol) were carefully mixed with 1,3-propane sultone and/or butane sultone(8.17 mmol), the reaction mixture was fused in an oil bath at140C for 0.5-4 h (thin-layer chromatography (TLC) control).The reaction mixture was then cooled to room temperature. Theobtainedsolidproductswerewashedfirstwithdiethylether,then triturated with ethanol and filtered off. The solid productswere recrystallized from diluted ethanol to give compounds2a-f,4a-g,and6a,b,respectively.
 

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