16937-91-0|H-D-Orn(Z)-OH| Ambeed

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Quality Control of [ 16937-91-0 ] Purity: 95% SDS Specification

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Product Details of [ 16937-91-0 ]

CAS No. :	16937-91-0
Formula :	C₁₃H₁₈N₂O₄
M.W :	266.29
SMILES Code :	O=C(O)[C@H](N)CCCNC(OCC1=CC=CC=C1)=O
MDL No. :	MFCD00063115
InChI Key :	VULSXQYFUHKBAN-LLVKDONJSA-N
Pubchem ID :	7272528

Safety of [ 16937-91-0 ]

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

Computational Chemistry of [ 16937-91-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	9
Num. H-bond acceptors	5.0
Num. H-bond donors	3.0
Molar Refractivity	69.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	101.65 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.6
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	-0.72
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.95
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.	-1.33
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	0.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.68
Solubility	56.0 mg/ml ; 0.21 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.94
Solubility	30.7 mg/ml ; 0.115 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.82
Solubility	0.401 mg/ml ; 0.00151 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.	-8.44 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.	0.55

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)	2.67

Application In Synthesis of [ 16937-91-0 ]

* 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 [ 16937-91-0 ]

[ 16937-91-0 ] Synthesis Path-Downstream 1~35

1
[ 16937-91-0 ]
[ 108-24-7 ]
[ 6205-08-9 ]

References: [1]Archives of Biochemistry,1956,vol. 64,p. 342,343.

2
[ 1070-19-5 ]
[ 16937-91-0 ]
[ 2480-93-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 2242 - 2249.

3
[ 70671-55-5 ]
[ 16937-91-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 575 - 576.

4
[ 16937-91-0 ]
[ 98-59-9 ]
[ 83160-02-5 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

6
copper (II)-salt of D-ornithine [ No CAS ]
[ 16937-91-0 ]

References: [1]Archives of Biochemistry,1956,vol. 64,p. 342,343.

7
[ 2480-93-5 ]
[ 16937-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol; at 0 - 20℃; for 18h;Inert atmosphere;	Boc-D-Orn(Cbz)-OH (400 mg, 1.09 mmol, 1.00 equiv) was dissolved in CH3OH (2.30 mL) at0 C. Then, freshly distilled thionylchloride (773 mg, 6.50 mmol, 5.95 equiv) was added dropwise. The reaction mixture was stirred at 0 C rt. After 18 h, the solvent was removed under reduced pressure. The resulting residue was charged with Et2O and the solvent was removed under reduced pressure. This procedure was repeated several times. The crudeproduct 22 was used without further purification.

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9045 - 9050.
[2]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 564 - 570.

8
[ 5874-56-6 ]
[ 16937-91-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 575 - 576.

9
[ 16937-91-0 ]
[ 83160-09-2 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

10
[ 16937-91-0 ]
N-((3S,6S,12R)-6-Benzyl-3-isobutyl-2,5,8,11-tetraoxo-1,4,7,10-tetraaza-cyclopentadec-12-yl)-4-methyl-benzenesulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

11
[ 16937-91-0 ]
[ 83160-08-1 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

12
[ 16937-91-0 ]
[(S)-1-((3S,6S,12R)-6-Benzyl-3-isobutyl-2,5,8,11-tetraoxo-1,4,7,10-tetraaza-cyclopentadec-12-ylcarbamoyl)-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

13
[ 16937-91-0 ]
H-Tyr-cyclo<-N^δ-D-Orn-Gly-Phe-Leu->*CH3COOH [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1432 - 1438.

14
[ 16937-91-0 ]
[ 16937-93-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 2242 - 2249.

15
[ 16937-91-0 ]
[ 28920-43-6 ]
[ 952729-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In dichloromethane;	Example 74A N5-[Benzyloxycarbonyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-ornithine N5-[(Benzyloxy)carbonyl]-D-ornithine (3.8 g, 14.27 mmol) [Ulhaq, Saraj et al.; Bioorg. Med. Chem.; EN; 7; 9; 1999; 1787-1796] is provided in dichloromethane (190 ml), DIEA (2.4 ml, 1.8 g, 17.27 mmol, 1 eq.) and chlorotrimethylsilane (3.6 ml, 3.1 g, 28.53 mmol, 2 eq.) are added, and the mixture is stirred under reflux overnight. The reaction is cooled (0 C.) and DIEA (4.7 ml, 3.7 g, 28.54 mmol, 2 eq.) again and (9-fluorenylmethyl) chloroformate (3.7 g, 14.27 mmol, 1 eq.) are added, and the mixture is warmed to RT and stirred at this temperature overnight. For the workup, the reaction is diluted with dichloromethane and washed with a 10% aq. citric acid solution, the organic phase is dried over sodium sulfate, the solvent is removed on a rotary evaporator and the mixture is dried in vacuo. 6.5 g (93.2% of theory) of the title compound are obtained. LC-MS (Method 18): Rt=2.57 min; MS (ESIpos): m/z (%)=489 (100) [M+H]+, 977 (100) [2M+H]+; MS (ESIneg.): m/z (%)=487 (80) [M-H]-, 975 (100) [2M-H]-.

References: [1]Patent: US2009/203582,2009,A1 .

16
[ 16937-91-0 ]
[ 82911-69-1 ]
[ 952729-12-3 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 8168 - 8172.

17
[ 16682-12-5 ]
[ 501-53-1 ]
[ 16937-91-0 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 8168 - 8172.

18
[ 24424-99-5 ]
[ 16937-91-0 ]
[ 2480-93-5 ]

Yield	Reaction Conditions	Operation in experiment
92%		Compound 5 (22 g, 82.6 mmol) was dissolved/suspended in an aqueous solution (250 mL) of potassium carbonate (12.56 g, 90.9 mmol) and 1,4-dioxane (100 mL) was added. Di-tert-butyl dicarbonate (18.93 g, 86.75 mmol) was added dropwise in 1,4-dioxane (200 mL) over a period of 60 min. The mixture was stirred at rt overnight, then concentrated under reduced pressure to a volume of about 150 mL. Water (50 mL) was added and the pH was adjusted to 2-3 by the addition of 1 M aq hydrochloric acid (about 150 mL). The product was extracted with ethyl acetate (400 mL and 3 × 300 mL) and the combined organic phases were treated with 10 mM aq hydrochloric acid (100 mL), saturated aq NH4Cl (200 mL), water (100 mL) as well as brine (250 mL) prior to drying over sodium sulfate. Filtration and evaporation of the solvent yielded a yellowish oil which turned into a foam that hardened to a solid during drying in vacuo (27.8 g, 92%). 1H NMR (300 MHz, DMSO-d6): delta (ppm) 1.38 (s, 9H), 1.4-1.59 (m, 3H), 1.65 (m, 1H), 2.98 (m, 2H), 3.83 (m, 1H), 5.0 (s, 2H), 7.07 (d, 1H, 3J = 8.0 Hz), 7.25 (t, 1H, 3J = 5.5 Hz), 7.34 (m, 5H), 12.42 (s, 1H); C18H28N2O6 (366.4).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

19
[ 16937-91-0 ]
[ 1310327-11-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

20
[ 16937-91-0 ]
[ 191868-52-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

21
[ 16937-91-0 ]
C₂₇H₃₇N₅O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

22
[ 16937-91-0 ]
[ 191855-71-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

23
[ 16937-91-0 ]
C₄₂H₄₉N₇O₇ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2859 - 2878.

24
[ 16937-91-0 ]
4-(3,5-dibromobenzyloxy)benzene-1-sulfonyl chloride [ No CAS ]
(R)-5-(benzyloxycarbonylamino)-2-(4-(3,5-dibromobenzyloxy)phenylsulfonamido)pentanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 8089 - 8103.

25
[ 32315-10-9 ]
[ 16937-91-0 ]
[ 13296-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 55℃;Inert atmosphere;	epsilon-Benzyloxycarbonyl ornithine N-Carboxyanhydride (ZOrn-NCA) was synthesized by following a literature procedure [44]. Briefly, ZOrn (5.00 g, 18.7 mmol) and triphosgene (3.50 g, 11.8 mmol) was suspended in 100 mL of dry THF under argon. The mixture was stirred in a 55 C oil bath until the cloudy solution turned clear. The solution was precipitated by addition of excess petroleum ether. The precipitate was collected by filtration and purified by recrystallization from ethyl acetate and petroleum ether. 1H NMR (300 MHz, CDCl3, delta): 7.35 (br s, C6H5), 5.09 (s, C6H5CH2), 4.32 (s, COCHNHCOO), 3.23 (s, CH2CH2CH2NHCOO), 1.95-1.61 (m, CHCH2CH2CH2NH).

References: [1]Polymer,2014,vol. 55,p. 4634 - 4640.

26
[ 16937-91-0 ]
4-(4-cyano-2-methylphenyl)piperazine-1-sulfonyl chloride [ No CAS ]
(R)-5-(benzyloxycarbonylamino)-2-(4-(4-cyano-2-methylphenyl)piperazine-1-sulfonamido)pentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With triethylamine; In tetrahydrofuran; water; at 20℃;	4.4 (R)-5-(Benzyloxycarbonylamino)-2-(4-(4-cyano-2-methylphenyl) piperazine-1-sulfonamido)pentanoic acid (6) To a solution of H-d-Orn(Z)-OH (270 mg, 1.00 mmol) in H2O (10 mL) containing Et3N (0.28 mL, 2.00 mmol), a solution of sulfonyl chloride 5 (300 mg, 1.00 mmol) in THF (10 mL) was added dropwise. The resulting mixture was stirred for 4 days at rt. The solvent was evaporated and the residue was treated with EtOAc (1 * 100 mL), washed with 1 N HCl (1 * 80 mL) and brine (1 * 80 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (CHCl3/MeOH 30:1) using a Isolute Flash Si II cartridge to give 6 as a white solid (80 mg, 15% yield). 1H NMR (400 MHz, DMSO-d6) delta: 1.50-1.69 (m, 4H), 2.27 (s, 3H), 2.97-3.03 (m, 6H), 3.15-3.23 (m, 4H), 3.66-3.72 (m, 1H), 5.00 (s, 2H), 7.11 (d, J = 8.9 Hz, 1H), 7.28-7.38 (m, 5H), 7.60-7.62 (m, 2H), 7.88 (d, J = 9.3 Hz, 1H), 12.77 (brs, 1H).

References: [1]European Journal of Medicinal Chemistry,2016,vol. 111,p. 193 - 201.

27
[ 16937-91-0 ]
[ 261927-30-4 ]
methyl (R)-5-[(benzyloxy)carbonyl]amino}-2-(2-iodo-3-methylbut-2-enamido)pentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	Boc-D-Orn(Cbz)-OH (400 mg, 1.09 mmol, 1.00 equiv) was dissolved in CH3OH (2.30 mL) at0 C. Then, freshly distilled thionylchloride (773 mg, 6.50 mmol, 5.95 equiv) was added dropwise. The reaction mixture was stirred at 0 C rt. After 18 h, the solvent was removed under reduced pressure. The resulting residue was charged with Et2O and the solvent was removed under reduced pressure. This procedure was repeated several times. The crudeproduct 22 was used without further purification. Acid 10 (138 mg, 0.61 mmol, 1.00 equiv) und amine 22 (222 mg, 0.79 mmol, 1.30 equiv)were dissolved in DMF (3.30 mL) at 0 C. Then, HOAt (88.7 mg, 0.65 mmol, 1.07 equiv) andPyAOP (333 mg, 0.64 mmol, 1.05 equiv) were added. Afterwards, DIPEA (361 mg, 2.79mmol, 4.59 equiv) was added dropwise. The reaction mixture was stirred at 0 C rt. After22 h, the reaction was terminated by adding a saturated NH4Cl solution. The layers wereseparated and the aqueous layer was extracted with EtOAc (7×). The combined organiclayers were washed with brine and subsequently dried over MgSO4 as well as filtered. Thesolvent was removed under reduced pressure. Purification by flash chromatography oversilica (petroleum ether/ethyl acetate = 3:1 petroleum ether/ethyl acetate = 1:1) yielded thedesired vinyl iodide 28 (197 mg, 0.40 mmol, 66% over two steps) as a colourless solid.

References: [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 564 - 570.

28
[ 16937-91-0 ]
[ 261927-30-4 ]
methyl (6S,12R)-12-(3-[(benzyloxy)carbonyl]amino}propyl)-6-isopropyl-2,2-dimethyl-4,7,10-trioxo-9-(propan-2-ylidene)-3-oxa-5,8,11-triazatridecan-13-oate [ No CAS ]

References: [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 564 - 570.

29
[ 16937-91-0 ]
[ 1093677-53-2 ]