147290-11-7|Fmoc-Orn(Aloc)-OH| Ambeed

Structure of Fmoc-Orn(Aloc)-OH
CAS No.: 147290-11-7

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Quality Control of [ 147290-11-7 ] Purity: 98% SDS Specification

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Product Details of [ 147290-11-7 ]

CAS No. :	147290-11-7
Formula :	C₂₄H₂₆N₂O₆
M.W :	438.47
SMILES Code :	O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CCCNC(OCC=C)=O
MDL No. :	MFCD00798637
InChI Key :	RXLIOYNXBHZZBI-NRFANRHFSA-N
Pubchem ID :	2756120

Safety of [ 147290-11-7 ]

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

Computational Chemistry of [ 147290-11-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	32
Num. arom. heavy atoms	12
Fraction Csp3	0.29
Num. rotatable bonds	14
Num. H-bond acceptors	6.0
Num. H-bond donors	3.0
Molar Refractivity	118.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	113.96 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.96
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	3.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.67
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.	2.32
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	3.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.28
Solubility	0.023 mg/ml ; 0.0000524 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.	-5.85
Solubility	0.000625 mg/ml ; 0.00000143 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-6.22
Solubility	0.000266 mg/ml ; 0.000000607 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	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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.31 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	1.0
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	2.0 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)	4.25

Application In Synthesis of [ 147290-11-7 ]

* 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 [ 147290-11-7 ]

[ 147290-11-7 ] Synthesis Path-Downstream 1~35

1
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 143824-78-6 ]
[ 147290-11-7 ]
N^α-Fmoc-Lys(N^ε-Boc)-OHWang resin-Val-Asp(Allyl)-Tyr(O-t-Bu)-NH2 [ No CAS ]
(S)-2-[(2S,5S,8S,11S,14S,21S)-5-(4-Amino-butyl)-21-((S)-2-amino-3-methyl-butyrylamino)-11-benzyl-2-(4-hydroxy-benzyl)-8-(1H-indol-3-ylmethyl)-3,6,9,12,19,22-hexaoxo-1,4,7,10,13,18-hexaaza-cyclodocosane-14-carbonyl]-amino}-succinic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3731 - 3739.

2
[ 209627-36-1 ]
[ 147290-11-7 ]
[ 854443-30-4 ]

References: [1]Tetrahedron,2005,vol. 61,p. 4901 - 4909.

3
[ 50-00-0 ]
[ 622-58-2 ]
[ 143824-78-6 ]
[ 147290-11-7 ]
3-(3-allyloxycarbonylamino-propyl)-4-oxo-2-<i>p</i>-tolylcarbamoyl-1,2,3,4,6,7,12,12b-octahydro-pyrazino[1',2':1,2]pyrido[3,4-<i>b</i>]indole-6-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 6843 - 6847.

4
[ 50-00-0 ]
[ 1476-23-9 ]
[ 143824-78-6 ]
[ 147290-11-7 ]
(3S,6S,12bS)-2-Allylcarbamoyl-3-(3-allyloxycarbonylamino-propyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-pyrazino[1',2':1,2]pyrido[3,4-b]indole-6-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 6843 - 6847.

5
[ 108-24-7 ]
[ 86123-10-6 ]
[ 133464-46-7 ]
[ 208465-10-5 ]
[ 147290-11-7 ]
N^α-Fmoc-His(Trt)-OHN^α-Fmoc-Trp(Boc)-OH [ No CAS ]
Ac-c[Glu-His-D-Phe-N^α-guanidinylbutyl-Orn]-Trp-NH2 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6888 - 6896.

6
[ 108-24-7 ]
[ 133464-46-7 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
[ 208465-10-5 ]
[ 147290-11-7 ]
N^α-Fmoc-His(Trt)-OHN^α-Fmoc-Trp(Boc)-OH [ No CAS ]
Ac-c[Glu-His-D-Nal(2)'-N^α-guanidinylbutyl-Orn]-Trp-NH2 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6888 - 6896.

7
[ 35661-60-0 ]
[ 71989-14-5 ]
[ 108-24-7 ]
[ 133464-46-7 ]
[ 147290-11-7 ]
Fmoc-L-Phe-(entagel resin) [ No CAS ]
Fmoc-L-Phe-OH [ No CAS ]
C₄₄H₅₈N₈O₁₄ [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 1201 - 1204.

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;	General procedure: Compound 5 (35.2 g, 0.135 mol) was added to a three-necked flask.Acetone (300 mL), water (300 mL),Sodium bicarbonate (22.7 g, 0.27 mol) and Fmoc-OSu (45.5 g, 0.135 mol) were then added.The reaction solution was stirred at room temperature for 12 hours.Petroleum ether extraction (500 mL3);The aqueous phase was acidified to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (500 mL EtOAc).The organic phases were combined and washed with saturated brine (500 mL).Dry over sodium sulfate and filter. Evaporate some of the ethyl acetate,Adding petroleum ether crystalline compound 6(N-fluorenylmethoxycarbonyl-N'-tert-butoxycarbonyl-homolysine)(57.3 g, yield 88%, HPLC purity:98.1%, ee: 99%).
		C. SYNTHESIS OF FMOC-ORN(ALOC)-OH. This amino acid derivative was prepared in the manner described above for lysine. Orn(AlOC)-OH . Ornithine hydrochloride [60 g; 0.375 moles] was dissolved in 800 mL of water and 9 g of NaOH was added. CuSO4 [47 g; 0.1875 moles] was added to this solution, whereupon the mixture became deep blue in color; it was stirred until all solids had dissolved. Next, 100 g of NaHCO3 was added, followed by allyl chloroformate [56.8 g; 0.4125 moles) in 300 mL of dioxane. The mixture bubbled and was stirred overnight. A sky blue solid was collected on a paper filter, and suspended in 2 L of hot water. H2S was bubbled through for 3 hours, and the black suspension was filtered and allowed to stand for 24 hours. The resulting yellow solution was concentrated to 500 mL and chilled overnight. White crystals were obtained and collected and washed with cold water. The mother liquor was further concentrated, yielding a second crop of crystals. Both batches appeared identical by TLC analysis (solvent system of ethyl acetate: pyridine: water: acetic acid, 35:20:11:6, vol/vol). The yield was 41.9 g (51.5% from Orn-HCl), mp 260C (decomposed). The product was analyzed by NMR and compositional analysis; results are shown below. 1H NMR (200 MHz, D 2 O) ppm : 6.0 - 5.7 (m) 1 H; 5.3 - 5.0 (m) 2 H; 4.5 - 4.4, (d) J = 5 Hz, 2 H; 3.7 - 3.5 (t) J = 7 Hz, 1 H; 3.2 - 3.0 (t) J = 6 Hz, 2 H; 1.9 - 1.6 (m) 2 H; 1.6 - 1.3 (m) 2 H. Analysis calculated for C8H16N2O4: C, 49.99. H, 7.45. N, 12.95. Analysis found: C, 50.09. H, 7.56. N, 13.14.

9
C₆₈H₉₁ClN₉O₉Pol [ No CAS ]
[ 147290-11-7 ]
C₉₁H₁₁₃ClN₁₁O₁₄Pol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3194 - 3202.

10
C₃₆H₄₅ClN₃O₄Pol [ No CAS ]
[ 147290-11-7 ]
C₆₀H₆₉ClN₅O₉Pol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3194 - 3202.

11
2-chlorotrityl chloride polystyrene resin [ No CAS ]
[ 147290-11-7 ]
C₄₃H₃₈ClN₂O₆Pol [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1843 - 1848.
[2]Journal of the American Chemical Society,2016,vol. 138,p. 3085 - 3093.

12
[ 225528-25-6 ]
[ 147290-11-7 ]
C₄₃H₄₇N₃O₇ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1340 - 1343.

13
[ 123-75-1 ]
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 71989-14-5 ]
[ 96989-50-3 ]
[ 64-19-7 ]
Nα-Fmoc-Nδ-(methyltrityl)-L-ornithine [ No CAS ]
[ 147290-11-7 ]
[ 1279698-76-8 ]