960225-75-6|5-Methyl-4-nitro-3-isoxazolecarboxylic acid| Ambeed

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Quality Control of [ 960225-75-6 ] Purity: 95% SDS Specification

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Product Details of [ 960225-75-6 ]

CAS No. :	960225-75-6
Formula :	C₅H₄N₂O₅
M.W :	172.10
SMILES Code :	O=C(C1=NOC(C)=C1[N+]([O-])=O)O
MDL No. :	MFCD11520861
InChI Key :	GIRMISJOXYRPLD-UHFFFAOYSA-N
Pubchem ID :	50998636

Safety of [ 960225-75-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 960225-75-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.2
Num. rotatable bonds	2
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	37.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	109.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.59
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	0.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.59
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.	-1.37
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	-1.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.37
Solubility	7.29 mg/ml ; 0.0424 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.	-2.32
Solubility	0.822 mg/ml ; 0.00478 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	-0.38
Solubility	72.4 mg/ml ; 0.421 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.	-7.02 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	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<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)	2.66

Application In Synthesis of [ 960225-75-6 ]

* 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 [ 960225-75-6 ]

[ 960225-75-6 ] Synthesis Path-Downstream 1~25

1
[ 960225-75-6 ]
5-methyl-4-nitroisoxazole-3-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20.0℃;Inert atmosphere;	<strong>[960225-75-6]5-methyl-4-nitroisoxazole-3-carboxylic acid</strong> (200 mg, 1.16 mmol) was dissolved in dichloromethane (4 ml) under argon atmosphere. Oxalyl chloride (202 muL, 2.32 mmol) was added dropwise at room temperature, followed by addition of one drop of DMF. After stirring overnight, the mixture was concentrated and co-evaporated with chloroform to afford 220 mg of 5 as a slightly yellow oil (1.15 mmol, 99%), which was carried on to the next step without further purification.

References: [1]Russian Chemical Bulletin,2005,vol. 54,p. 2813 - 2819.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1822 - 1826.

2
[ 3405-77-4 ]
[ 960225-75-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sulfuric acid; potassium nitrate; at 50.0℃; for 4.0h;	5-methylisoxazole-3-carboxylic acid (1.5 g, 12.04 mmol) was added to a mixture of potassium nitrate (1.83 g, 18.06 mmol) and sulfuric acid (5 ml) at room temperature. After complete dissolution, the mixture was warmed to 50C and stirred for 4 hours. The mixture was then cooled to 0C, ice was added, and the solution was neutralized with sodium bicarbonate. The mixture was extracted with ethyl acetate (3 x 30 ml), dried over sodium sulfate, filtered and concentrated to give 1.45 g of 4 as a white solid (8.43 mmol, 70%). The product could be further recrystallized from dichloromethane.
51.6 g	With sodium nitrate; sulfuric acid; at 50.0℃; for 16.0h;	A) 5-Methyl-4-nitro-1,2-oxazole-3-carboxylic acid To a solution of 5-methyl-1,2-oxazole-3-carboxylic acid (50.84 g) in concentrated sulfuric acid (500 mL), sodium nitrate (50.99 g) was gradually added at room temperature. The reaction mixture was stirred at 50C for 16 hours. After cooling to room temperature, the reaction solution was gradually added to ice, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine and then dried over anhydrous sodium sulfate to obtain the title compound (51.6 g). 1H NMR (400 MHz, DMSO-d6) delta 2.28 (3H, s), 10.66 (1H, brs).

References: [1]Russian Chemical Bulletin,2005,vol. 54,p. 2813 - 2819.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1822 - 1826.
[3]Patent: EP3287441,2018,A1 .Location in patent: Paragraph 0329.

3
[ 960225-75-6 ]
[ 904441-37-8 ]