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Chemical Structure| 5718-83-2 Chemical Structure| 5718-83-2

Structure of 5718-83-2

Chemical Structure| 5718-83-2

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Product Details of [ 5718-83-2 ]

CAS No. :5718-83-2
Formula : C5H5NO3S2
M.W : 191.23
SMILES Code : O=C(O)CN1C(SCC1=O)=S
MDL No. :MFCD00005491
InChI Key :JGRMXPSUZIYDRR-UHFFFAOYSA-N
Pubchem ID :79793

Safety of [ 5718-83-2 ]

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

Computational Chemistry of [ 5718-83-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 48.2
TPSA ?

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

115.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.84
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

0.45
Log Po/w (WLOGP)?

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

-0.45
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.

-1.03
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

1.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.22

Water Solubility

Log S (ESOL):?

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

-1.18
Solubility 12.7 mg/ml ; 0.0665 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.

-2.43
Solubility 0.705 mg/ml ; 0.00369 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

0.08
Solubility 230.0 mg/ml ; 1.2 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.

-7.15 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.

0.56

Medicinal Chemistry

PAINS?

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

1.0 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)

2.57

Application In Synthesis of [ 5718-83-2 ]

* 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 [ 5718-83-2 ]

[ 5718-83-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 5718-83-2 ]
  • [ 33985-71-6 ]
  • C18H18N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With ammonium acetate; acetic acid; at 120℃; for 0.5h; Compound (F-2) (1.0 g), rhodanine-3-acetic acid (0.96 g) and ammonium acetate (0.4 g) were dissolved in 2.0 g of acetic acid, and the mixture was stirred under heat at 120C. After 30 minutes, when the heating was stopped, the reaction product immediately solidified. The reaction product was cooled to room temperature, and then, water (50 ml) was added. The mixture was stirred, and a crystal was recovered by filtration. The crystal was transferred into a beaker and washed with water (200 ml). The crude crystal was re-crystallized from methyl cellosolve, to give Compound (A-5) shown as an example. 1.3 g. Yield 70 %.
  • 2
  • [ 5718-83-2 ]
  • [ 5780-66-5 ]
  • [(5Z)-4-oxo-5-(pyrazin-2-ylmethylene)-2-thioxo-1,3-thiazolidin-3-yl]acetic acid [ No CAS ]
  • 3
  • [ 5718-83-2 ]
  • [ 54117-37-2 ]
  • C25H18N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With pyridine; In ethanol; at 80℃; for 4h; The above-prepared compound A34 and 1.1 equivalents of rhodamine 3-acetic acid were dissolved in ethanol, one equivalent of pyridine was added, and the reaction was carried out at 80 C. for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature to precipitate a yellow solid, which was suction-filtered and the filter cake was diluted. After washing with hydrochloric acid, washing with water, infrared drying, and then recrystallization with ethanol gave a yellow solid with a yield of 80%.
  • 4
  • [ 5718-83-2 ]
  • [ 54117-37-2 ]
  • (Z)-2-(5-((9-benzyl-9H-carbazol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium acetate; acetic acid; at 110℃; for 4h; General procedure: A mixture of the appropriate aldehydes (2a-2m, 0.1 mmol), the rhodanine-3-acetic acid (0.1 mmol), and NaOAc (0.3 mmol) in acetic acid (6 mL) heated to 110 C for 4h. Then, it was cooled to room temperature and poured into water. The product was then filtered through the suction pump, washed with water/EtOH (1/1, v/v) to remove the excess acetic acid and recrystallized from EtOH and finally a yellow solid was obtained for 3a-3m in66-91% yields.
  • 5
  • [ 5718-83-2 ]
  • [ 87220-68-6 ]
  • (Z)-2-(4-oxo-5-((9-phenyl-9H-carbazol-3-yl)methylene)-2-thioxothiazolidin-3-yl)acetic acid [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 5718-83-2 ]

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Related Parent Nucleus of
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