27486-87-9|Ac-Cys(Trt)-OH| Ambeed

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Quality Control of [ 27486-87-9 ] Purity: 97% SDS Specification

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Product Details of [ 27486-87-9 ]

CAS No. :	27486-87-9
Formula :	C₂₄H₂₃NO₃S
M.W :	405.51
SMILES Code :	O=C(O)[C@@H](NC(C)=O)CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :	MFCD00236747
InChI Key :	KCVPASSMLHHOIF-QFIPXVFZSA-N
Pubchem ID :	7408363

Safety of [ 27486-87-9 ]

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

Computational Chemistry of [ 27486-87-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	29
Num. arom. heavy atoms	18
Fraction Csp3	0.17
Num. rotatable bonds	9
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	116.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	91.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.56
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.19
Log P_o/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.	3.83
Log P_o/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	4.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.92

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.05
Solubility	0.00363 mg/ml ; 0.00000895 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.	-6.14
Solubility	0.000296 mg/ml ; 0.000000731 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	-7.72
Solubility	0.00000769 mg/ml ; 0.000000019 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	Yes
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	Yes
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.	-5.59 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.	0.56

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)	3.82

Application In Synthesis of [ 27486-87-9 ]

* 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 [ 27486-87-9 ]

[ 27486-87-9 ] Synthesis Path-Downstream 1~35

1
[ 6066-82-6 ]
[ 27486-87-9 ]
[ 73609-53-7 ]

References: [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 696 - 698.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 1789 - 1795.
[3]Journal of the American Chemical Society,2013,vol. 135,p. 2088 - 2091.

2
[ 76-84-6 ]
N-acetyl-L-cysteine hydrochloride [ No CAS ]
[ 27486-87-9 ]

References: [1]Journal of Medicinal Chemistry,1970,vol. 13,p. 414 - 418.

3
[ 541-41-3 ]
[ 27486-87-9 ]
C₂₇H₂₇NO₅S [ No CAS ]

References: [1]Liebigs Annales,1996,p. 841 - 843.

4
[ 616-91-1 ]
[ 76-83-5 ]
[ 27486-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20℃;	N-Acetyl-cysteine (100.0 g, 613 mmol) was dissolved in DMF (600 mL) andtriphenylmethyl chloride (179.4 g, 643 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with water andextracted twice with ethyl acetate. The combined organic layers were washed withbrine, dried over sodium sulfate and filtered. The solvent was removed in vacuo to givecompound 2-1. lodoethane (144.3 g, 925 mmol) was added to a suspension of 2-1(250.0 g, 617 mmol) and K2003 (170.4 g, 1233 mmol) in DMF (1250 ml). The reaction mixture was stirred at room temperature overnight then diluted with ice-water andextracted twice with ethyl acetate. The combined organic layers were washed withwater, brine, dry over sodium sulfate and filtered. The solvent was removed from the filtrate in vacuo to give compound 2-2. TFA (480 mL) was added to a solution of 2-2 (240 g, 554 mmol) and triethylsilane (128.7 g, 1107 mmol) in dichloromethane (2.4 L) at 0 00 and the reaction mixture allowed to stir at room temperature overnight. Thesolvent was removed in vacuo and compound 2-3 isolated by column chromatography.

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2209 - 2218.
[2]Tetrahedron Letters,1997,vol. 38,p. 2149 - 2152.
[3]Liebigs Annales,1996,p. 841 - 843.
[4]Patent: WO2017/60420,2017,A1 .Location in patent: Page/Page column 34; 35; 36.
[5]RSC Advances,2018,vol. 8,p. 2818 - 2823.

5
[ 13518-40-6 ]
[ 27486-87-9 ]
(S)-2-((R)-2-Acetylamino-3-tritylsulfanyl-propionylamino)-3-methyl-butyric acid tert-butyl ester [ No CAS ]

References: [1]Chemische Berichte,1996,vol. 129,p. 1243 - 1249.

6
[ 4530-20-5 ]
[ 29022-11-5 ]
[ 27486-87-9 ]
[ 191277-10-8 ]
FmocCys(Trt)OH, BocGlu(OH)OtBu [ No CAS ]
(S)-4-((4R,23R)-23-Acetylamino-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaaza-cyclotetracos-4-ylcarbamoyl)-2-amino-butyric acid [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 17317 - 17334.

7
[ 27486-87-9 ]
[ 543-27-1 ]
C₂₉H₃₁NO₅S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1189 - 1191.
[2]Bioorganic Chemistry,2008,vol. 36,p. 133 - 140.

8
[ 62-31-7 ]
[ 27486-87-9 ]
[ 906666-23-7 ]

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.

9
[ 2799-07-7 ]
[ 108-24-7 ]
[ 27486-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 20℃; for 1h;	General procedure: Acetic anhydride (6.6 mmol) was added to a stirred solutionof alkylated cysteine derivatives (5.5 mmol) in acetic acid (11.1 mL) and the reaction mixture was left under stirring at room temperature for 1 h. The solvent was removed under vacuum giving the corresponding N-acetylated amino acids which were used without further purification.

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.
[2]Journal of the American Chemical Society,2013,vol. 135,p. 2088 - 2091.
[3]PLoS ONE,2015,vol. 10.

10
[ 76-83-5 ]
sodium benzylate [ No CAS ]
[ 27486-87-9 ]

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.

11
[ 27486-87-9 ]
N-(3,4-dihydroxyphenethyl)-2-acetamido-3-mercaptopropanamide [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.

12
[ 27486-87-9 ]
2-acetylamino-3-mercapto-<i>N</i>-(2-mercapto-ethyl)-propionamide [ No CAS ]