Boc-Ser(Bzl)-OH | N-protective Amino Acid

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Quality Control of [ 23680-31-1 ] Purity: 98% SDS Specification

COA

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Product Details of [ 23680-31-1 ]

CAS No. :	23680-31-1
Formula :	C₁₅H₂₁NO₅
M.W :	295.33
SMILES Code :	O=C(O)[C@@H](NC(OC(C)(C)C)=O)COCC1=CC=CC=C1
Synonyms :	(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid
MDL No. :	MFCD00066063

Safety of [ 23680-31-1 ]

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

Computational Chemistry of [ 23680-31-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	6
Fraction Csp3	0.47
Num. rotatable bonds	9
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	77.23
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.	2.58
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	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.03
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.	1.41
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	1.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.49
Solubility	0.966 mg/ml ; 0.00327 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.	-3.3
Solubility	0.146 mg/ml ; 0.000496 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	-3.31
Solubility	0.144 mg/ml ; 0.000488 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.	-6.75 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)	3.21

Application In Synthesis of [ 23680-31-1 ]

* 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 [ 23680-31-1 ]

[ 23680-31-1 ] Synthesis Path-Downstream 1~42

1
[ 23680-31-1 ]
[ 2886-33-1 ]
[ 127103-15-5 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2122 - 2127.

2
[ 23680-31-1 ]
[ 501-53-1 ]
[ 20806-43-3 ]

References: [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 935 - 943.

3
[ 23680-31-1 ]
[ 40350-83-2 ]
(±)-1-azafagomine [ No CAS ]
[ 541-88-8 ]
(2S,4R)-1-{(2S,4R)-1-[2-(4,5-Dihydroxy-3-hydroxymethyl-tetrahydro-pyridazin-1-yl)-acetyl]-4-hydroxy-pyrrolidine-2-carbonyl}-4-hydroxy-pyrrolidine-2-carboxylic acid ((S)-1-carbamoyl-2-hydroxy-ethyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 1965 - 1971.

4
[ 15761-39-4 ]
[ 13734-41-3 ]
[ 13139-15-6 ]
[ 15761-38-3 ]
C₁₆H₂₈N₃O₅PolS [ No CAS ]
[ 7536-55-2 ]
[ 13726-85-7 ]
[ 13574-13-5 ]
[ 13836-37-8 ]
[ 23680-31-1 ]
[ 47355-10-2 ]
[ 83468-83-1 ]
Fmoc-Asp-Cys(Acm)-His-Leu-Gln-Ala-Val-Val-Leu-His-Leu-Ala-Arg-Arg-Ser-Val-Cys(Acm)-Val-His-Pro-Gln-Asn-Arg-Ser-Leu-Ala-Arg-Trp-Leu-Glu-Arg-Gln-Gly-S-CH₂CH₂CO-Leu-NH₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1808 - 1813.

5
[ 4530-20-5 ]
[ 15761-39-4 ]
[ 13139-15-6 ]
C₁₄H₁₄NPol [ No CAS ]
[ 13836-37-8 ]
[ 23680-31-1 ]
[ 47689-67-8 ]
[ 47355-10-2 ]
[ 53100-44-0 ]
[ 35899-43-5 ]
[ 33515-09-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The peptides were synthesized manually accordingly to the standard Boc protocol [1] and [3]. In the Boc chemistry, after coupling the C-terminal amino acid to the resin, the successive alpha-amino group deprotection and neutralization steps were performed in 30% TFA/DCM (30 min) and 10% TEA/DCM (10 min). The amino acids were coupled with 3-fold excess, using DIC/HOBt in DMF and, if necessary, Boc-amino acid/(N-[(1H-benzotriazol-1-yl)-(dimethylaminomethylene)]-N-methylmethanaminium hexafluorophosphate N-oxide (HBTU)/HOBt (1:1:1), in the presence of excess of diisopropylethylamine (DIEA, 5 equiv.) using 20% DMSO/NMP as the solvent system. After a 3-h coupling period, the qualitative ninhydrin test was performed to estimate the completeness of the reaction. To check the purity of the synthesized peptide sequence attached to the resin, cleavage reactions with small aliquots of resin were carried out in anhydrous HF, at 0 C for 2 h.

References: [1]Bioorganic Chemistry,2011,vol. 39,p. 101 - 109.

6
[ 15761-39-4 ]
[ 13139-15-6 ]
[ 15761-38-3 ]
[ 13836-37-8 ]
[ 23680-31-1 ]
[ 73821-95-1 ]
[ 54613-99-9 ]
[ 47689-67-8 ]
[ 47355-10-2 ]
[ 83468-83-1 ]
[ 65420-40-8 ]
HSQGTFTSDYSKYLDSRRAQDFVQWLMNGGPSSGAPPPS-NH₂ [ No CAS ]