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Quality Control of [ 96402-49-2 ] Purity: 98% SDS Specification

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NMR

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Product Details of [ 96402-49-2 ]

CAS No. :	96402-49-2
Formula :	C₂₈H₂₃NO₄
M.W :	437.49
MDL No. :	MFCD00151914
InChI Key :	ORWNVJDLEMVDLV-SANMLTNESA-N
Pubchem ID :	2734474

Safety of [ 96402-49-2 ]

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

Calculated chemistry of [ 96402-49-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	33
Num. arom. heavy atoms	22
Fraction Csp3	0.14
Num. rotatable bonds	8
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	127.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	75.63 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.8
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	5.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.37
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.	4.06
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	5.09
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.23
Solubility	0.000259 mg/ml ; 0.000000591 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-7.25
Solubility	0.0000245 mg/ml ; 0.000000056 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	-9.01
Solubility	0.00000043 mg/ml ; 0.000000001 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	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.	-4.79 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.	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)	4.18

Application In Synthesis [ 96402-49-2 ]

* 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 [ 96402-49-2 ]

[ 96402-49-2 ] Synthesis Path-Downstream 1~24

1
[ 28920-43-6 ]
[ 55516-54-6 ]
[ 96402-49-2 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2 - 10

2
[ 108-24-7 ]
[ 91000-69-0 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Ac-His-Nal(1')-Arg-Trp-NH₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3073 - 3081

3
[ 108-24-7 ]
[ 86123-10-6 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
Fmoc-Arg(Pbf)-OH [ No CAS ]
Ac-His-D-Phe-Arg-Nal(1')-NH₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5736 - 5744

4
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(R)-N-α-Fmoc-N-ε-Boc-lysinal [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055

5
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(S)-N-α-Fmoc-N-ε-Boc-lysinal [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055

6
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(S)-N-α-Fmoc-N-ε,N-γ-di-Boc-arginal [ No CAS ]
(S)-2-{(R)-6-(3-Guanidino-propyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]
(S)-2-{(R)-6-(3-Guanidino-propyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055

7
[ 29022-11-5 ]
[ 96402-49-2 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-thienyl)propanoic acid [ No CAS ]
Fmoc-Arg(Pbf)-Wang resin [ No CAS ]
C₇₀H₉₁N₁₉O₁₂S₂ [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2003,vol. 77,p. 881 - 887

8
[ 96402-49-2 ]
[ 4942-47-6 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline [ No CAS ]
Fmoc-Arg(Pbf)-Wang resin [ No CAS ]
C₈₂H₁₀₇N₁₉O₁₃S₂ [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2003,vol. 77,p. 881 - 887

9
[ 68858-20-8 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 96402-49-2 ]
Fmoc-Tyr(t-Bu)-NH-resin [ No CAS ]
(S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Amino-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carbonyl}-amino)-3-naphthalen-1-yl-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

10
[ 67-56-1 ]
[ 71989-14-5 ]
[ 96402-49-2 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
(S)-3-[1-(2-Hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-N-[(S)-1-(methoxycarbonylmethyl-carbamoyl)-2-naphthalen-1-yl-ethyl]-succinamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 10676 - 10681

11
[ 67-56-1 ]
[ 96402-49-2 ]
[ 77284-32-3 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
[(S)-2-((S)-2-[1-(2-Hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-acetic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 10676 - 10681

12
[ 591-80-0 ]
[ 29022-11-5 ]
[ 96402-49-2 ]
((S)-3-Naphthalen-1-yl-2-pent-4-enoylamino-propionylamino)-acetic acid [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2695 - 2698

13
[ 112883-29-1 ]
[ 96402-49-2 ]
[ 73731-37-0 ]
[ 35737-15-6 ]
N-Fmoc-L-Pro-2-chlorotrityl polystyrene resin [ No CAS ]
N-Fmoc-L-Phe [ No CAS ]
cyclo(1-Nal-D-Trp-Tyr-Thr-Phe-Pro) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 551 - 559

14
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 2491-06-7 ]
[ 96402-49-2 ]
piperazine [ No CAS ]
C₃₅H₄₄N₆O₄ [ No CAS ]

Reference： [1]Organic Letters,1999,vol. 1,p. 345 - 347

15
[ 96402-49-2 ]
C₃₆H₄₆N₆O₄ [ No CAS ]

Reference： [1]Organic Letters,1999,vol. 1,p. 345 - 347

16
[ 96402-49-2 ]
C₃₆H₅₄N₆ [ No CAS ]

Reference： [1]Organic Letters,1999,vol. 1,p. 345 - 347

17
[ 35661-40-6 ]
[ 96402-49-2 ]
[ 183673-66-7 ]
C₇₃H₇₈N₁₁O₁₀Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Each of the reaction wells contained 0.0675 mmol of Rink Amide MBHA resin(substitution = 0.72 mmol/g, Novabiochem, San Diego, CA). The following Fmoc amino acids (Novabiochem, San Diego, CA; Chem-Impex International, Wood Dale, IL; SyntheTech, Albany, OR; Pharma Core, High Point, NC) were used: Fmoc-Lys(Boc)-OH, EPO <DP n="112"/>Fmoc-Phe-OH, Fmoc-H-Inp-OH, Fmoc-D-lNal-OH, Fmoc-D-2Nal-OH, Fmoc-D- TrP(BoC)-OH, Fmoc-3Pal-OH, Fmoc-4Pal-OH/ FmOc-Om(BoC)-OH, Fmoc-D-Bip-OH, FmOC-ThT(BzI)-OH, Fmoc-Pff-OH, Fmoc-2Thi-OH, Fmoc-Taz-OH, Fmoc-D-Dip-OH, Fmoc-D-Bpa-OH, Fmoc-D-Bal-OH, and Fmoc-Apc(Boc)-OH.Each of the Fmoc amino acids was dissolved in a 0.3 N solution of HOBt in DMF wherein the concentration of the resulting Fmoc amino acid was 0.3 N. A four fold excess (0.27 mmol, 0.9 mL of the 0.3 N solution) of Fmoc amino acid was used for each coupling. DIC (0.27 mmol, 0.6 mL of 0.45N DIC solution in DMF) was used as the coupling reagent for each coupling. Deprotection was performed by using 20percent piperidine in DMF (2 X 1.5 mL per residue). The peptides were cleaved from the resin by treating the peptide-resins with 8percent trsopropylsilane (TIP) in trifluoroacetic acid (TFA) (1.5 mL per reaction well) at room temperature for 2h. The resin was removed by filtration. Each filtrate was diluted to 25 mL with ether in a centrifuge tube. The resulting precipitate in each tube was centrifuged and the solvents were decanted from the precipitate. The precipitate in each tube was then dissolved in methanol (3 mL) and diluted with water (1 mL). The purification of the crude products was done on a reverse-phase preparative HPLC using a column (100 X 21.20 mm, 5mu) of LUNA 5mu C8(2) (Phenomenex, Torrance, CA). For each peptide, the column was eluted with a linear gradient from 85percent A and 15percent B to 25percent A and 75percent B in 15 min with a flow rate of 25 mL/min. A was 0.1percent TFA in water and B was 0.1percent TFA in acetonitrile/water (80/20, v/v). The fractions were checked by analytical HPLC and those containing the pure product were combined and lyophilized to dryness.Yields ranged from 13percent to 71percent and purity of each of Examples 1 - 65 exceeded 94percent based upon analytical HPLC analysis. Electro-spray ionization mass spectrometry (ES-MS) analysis was performed and observed molecular weights were in agreement with calculated molecular weights. The results are detailed in Table I, below

Reference： [1]Patent: WO2007/41278,2007,A2 .Location in patent: Page/Page column 110-111

18
[ 96402-49-2 ]
[ 252279-09-7 ]
C₄₇H₃₉N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In dichloromethane; for 0.166667h;	The forgoing solution of the intermediate product IB was divided into four equal portions and coupled with the pre-activated HOBT esters of FMOC protected amino acids, as summarized in reaction schemes 1C, ID, IE, and IF, below. The amino acid used: FMOC-D-2Nal-OH (130mg, 0.30mmole) (Synthetech Albany, Oregon) Each of the immediately foregoing amino acids was pre-activated with HOBT (46mg, 0.30mmole) and DIC (38mg, 0.30mmole) in DCM (5ml) for ten minutes before addition to one of the four portions of the forgoing solution of the intermediate product IB. The coupling reaction was then allowed to proceed for 30 minutes at room temperature.

Reference： [1]Patent: WO2007/41278,2007,A2 .Location in patent: Page/Page column 113-114

19
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₇₅H₂₁₄N₂₁O₂₄PolS₃ [ No CAS ]