159610-93-2|(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxypropanoic acid| Ambeed

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Quality Control of [ 159610-93-2 ] Purity: 98% SDS Specification

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Product Details of [ 159610-93-2 ]

CAS No. :	159610-93-2
Formula :	C₁₉H₁₉NO₅
M.W :	341.36
SMILES Code :	O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)COC
MDL No. :	MFCD02682604
InChI Key :	YFWAFELGMGZCHL-KRWDZBQOSA-N
Pubchem ID :	46737425

Safety of [ 159610-93-2 ]

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

Computational Chemistry of [ 159610-93-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	25
Num. arom. heavy atoms	12
Fraction Csp3	0.26
Num. rotatable bonds	8
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	91.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.41
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	2.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.62
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.	1.74
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	2.47
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.36

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.38
Solubility	0.141 mg/ml ; 0.000413 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.	-3.97
Solubility	0.0367 mg/ml ; 0.000107 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	-5.02
Solubility	0.00324 mg/ml ; 0.00000951 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	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.	-6.58 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<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)	3.9

Application In Synthesis of [ 159610-93-2 ]

* 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 [ 159610-93-2 ]

[ 159610-93-2 ] Synthesis Path-Downstream 1~35

1
[ 28920-43-6 ]
[ 159610-93-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of L-serine (methyl ether) hydrochloride (069) (1.0 g, 6.4 mmol) in water/dioxane (1:1, 80 ml) was added sodium hydroxide (768 mg, 19.2 mmol). After the mixture was stirred at room temperature for 30 minutes, it was cooled to 0 ° C., and a solution of 9-fluorenylmethyl chloroformate (1.65 g, 6.4 mmol) in dioxane (16 mL) was added dropwisely. The reaction mixture was allowed to stir at room temperature for another 4 hours. The solvents were then removed, the residue was diluted with water and the pH was adjusted to 1 with 1N HCl, and the aqueous layer was extracted with ethyl acetate (4.x.100 mL). The organic layers were concentrated under reduced pressure and placed under high vacuum to provide (070) (1.8 g) as confirmed by LC/MS (LCRS (MH) m/z: 342.13) which was used without further purification.

References: [1]Patent: US2007/105786,2007,A1 .Location in patent: Page/Page column 33; 34.

2
[ 159610-93-2 ]
HMPB-BHA resin [ No CAS ]
C₄₄H₄₃N₂O₈Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-1H-imidazole; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole; In dichloromethane;	The resin HMPB-BHA (500 mg, 0.32 mmol ) was washed with dichloromethane. In a dry flask, <strong>[159610-93-2]Fmoc-Ser(Me)-OH</strong> (070) (546 mg, 1.6 mmol) was dissolved in dichloromethane and to the solution was added 1-methylimidazole (95 muL, 1.2 mmol) followed by MSNT (474 mg, 1.6 mmol). Once the resulting mixture had become homogenous (10 minutes) it was added to the HMPB-BHA resin as a suspension in dichloromethane (5 mL). The resulting reaction mixture was allowed to shake overnight. The resin was then filtered off and washed with DMF (3.x.20 mL), MeOH (3.x.20 mL), DCM (3.x.20 mL), and allowed to air dry to yield (071).

References: [1]Patent: US2007/105786,2007,A1 .Location in patent: Page/Page column 33; 34.

3
fmoc-Leu-Alko Resin [ No CAS ]
[ 159610-93-2 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 64-19-7 ]
Ac-PLG-S(OMe)YL [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856.

4
[ 159610-93-2 ]
H-cysteine(trityl)-2-chlorotrityl resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 67436-13-9 ]
[ 119831-72-0 ]
FFC(Acm)PFGC(t-Bu)ALVDCGPNRPC(t-Bu)RDTGF-(L-O-methylhomoserinyl)-SC(Acm)DC [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1476 - 1481.

5
[ 50-00-0 ]
[ 159610-93-2 ]
C₂₀H₁₉NO₅ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 7043 - 7052.

6
[ 159610-93-2 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Fmoc-Arg(pg)-OH [ No CAS ]
H-His-Ser(Me)-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Leu-Ser-Lys-Gln-Met-Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Ile-Glu-Trp-Leu-Lys-Asn-Gly-Gly-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Ser-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The solid phase peptide syntheses were performed on a Prelude Peptide Synthesizer (Protein Technologies Inc) using standard Fmoc chemistry and HBTU/DIPEA activation. DMF was used as the solvent. Deprotection: 20percent piperidine/DMF for 2×2.5 min. Washes: 7×DMF. Coupling 2:5:10 200 mM AA/500 mM HBTU/2M DIPEA in DMF 2× for 20 min. Washes: 5×DMF. In cases where a Lys-side-chain was modified, Fmoc-L-Lys(ivDde)-OH was used in the corresponding position. After completion of the synthesis, the ivDde group was removed according to a literature procedure (S. R. Chhabra et al., Tetrahedron Lett. 39, (1998), 1603). The following acylations were carried out by treating the resin with the N-hydroxy succinimide esters of the desired acid or using coupling reagents like HBTU/DIPEA or HOBt/DIC. (0270) All the peptides that had been synthesized were cleaved from the resin with King's cleavage cocktail consisting of 82.5percent TFA, 5percent phenol, 5percent water, 5percent thioanisole, 2.5percent EDT. The crude peptides were then precipitated in diethyl or diisopropyl ether, centrifuged, and lyophilized. Peptides were analyzed by analytical HPLC and checked by ESI mass spectrometry. Crude peptides were purified by a conventional preparative HPLC purification procedure. Example 1 The solid phase synthesis was carried out on Rink-resin with a loading of 0.38 mmol/g, 75-150 mum from the company Agilent Technologies. The Fmoc-synthesis strategy was applied with HBTU/DIPEA-activation. The peptide was cleaved from the resin with King's cocktail (D. S. King, C. G. Fields, G. B. Fields, Int. J. Peptide Protein Res. 36, 1990, 255-266). The crude product was purified via preparative HPLC on a Waters column (XBridge, BEH130, Prep C18, 5 muM) using an acetonitrile/water gradient (both buffers with 0.1percent TFA). (0296) Finally, the molecular mass of the purified peptide was confirmed by LC-MS. M.W. (calculated)=4188.5 g/mol; M.W. (found)=4188.6 g/mol.

References: [1]Patent: US9181305,2015,B2 .Location in patent: Page/Page column 58; 59; 62; 63; 69; 70.

7
[ 159610-93-2 ]
[ 35661-39-3 ]
Fmoc-L-Lys(iPr,Boc)-OH [ No CAS ]
[ 35661-40-6 ]
[ 71989-38-3 ]
HO-Phe-Tyr(tBu)-Ser(Me)-Ala-Lys(iPr,Boc)-NH2 [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 506 - 509.

8
[ 159610-93-2 ]
[ 35661-39-3 ]
Fmoc-Lys(Cbz)-OH [ No CAS ]
[ 112883-29-1 ]
[ 35661-40-6 ]
HO-Ala-Lys(Cbz)-Phe-Tyr-Ser(Me)-NH2 [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 506 - 509.

9
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid [ No CAS ]
[ 159610-93-2 ]
[ 35661-40-6 ]
[ 132388-59-1 ]
[ 77128-72-4 ]
HO-Phe-Tyr(Me)-Ser(Me)-Asn(Trt)-Lys(Me)2-NH2 [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 506 - 509.

10
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid [ No CAS ]
[ 159610-93-2 ]
[ 132388-59-1 ]
[ 77128-72-4 ]
HO-Ser(Me)-Asn(Trt)-Lys(Me)2-Asn(Trt)-Tyr(Me)-NH2 [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 506 - 509.

11
[ 3235-69-6 ]
[ 159610-93-2 ]
C₂₆H₁₉N₂O₅Pol [ No CAS ]
[ 132684-59-4 ]
[ 95753-56-3 ]
Mor-Hfe-Ser(Me)-Phe(4-NH₂)-ACC [ No CAS ]