16600-92-3|2-Nitrobenzene-1,3,5-triol| Ambeed

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Quality Control of [ 16600-92-3 ] Purity: 95% SDS Specification

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Product Details of [ 16600-92-3 ]

CAS No. :	16600-92-3
Formula :	C₆H₅NO₅
M.W :	171.11
SMILES Code :	OC1=CC(O)=CC(O)=C1[N+]([O-])=O
MDL No. :	MFCD00016996
InChI Key :	QSVQZFVXAUGEMT-UHFFFAOYSA-N
Pubchem ID :	85509

Safety of [ 16600-92-3 ]

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

Computational Chemistry of [ 16600-92-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	5.0
Num. H-bond donors	3.0
Molar Refractivity	41.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	106.51 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.42
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	1.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.71
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.	-0.85
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	-1.7
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.33
Solubility	0.796 mg/ml ; 0.00465 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.	-3.65
Solubility	0.0387 mg/ml ; 0.000226 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	-0.05
Solubility	153.0 mg/ml ; 0.893 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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.07 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.	0.55

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	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)	1.75

Application In Synthesis of [ 16600-92-3 ]

* 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 [ 16600-92-3 ]

[ 16600-92-3 ] Synthesis Path-Downstream 1~35

1
[ 186581-53-3 ]
[ 16600-92-3 ]
[ 14227-18-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1928,vol. 460,p. 23.

2
[ 99-35-4 ]
[ 16600-92-3 ]
9-hydroxy-4,8,10,11-tetranitro-tricyclo[5.3.1.1^2,6]dodecane-3,5,12-trione [ No CAS ]

References: [1]Chemische Berichte,1959,vol. 92,p. 1517,1518.

3
[ 108-73-6 ]
[ 16600-92-3 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 6818 - 6825.
[2]Tetrahedron,2011,vol. 67,p. 6746 - 6752.
[3]Justus Liebigs Annalen der Chemie,1861,vol. 119,p. 201.
[4]Journal of Organic Chemistry,1954,vol. 19,p. 1359.

4
[ 16600-92-3 ]
[ 139173-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;	Example 1 : Chemical synthesis of compound 1 D; Nitrophloroglucinol (1 g, 6.5 mMol) was dissolved in 10 ml of methanol and hydrogenated in a hydrogen atmosphere in the presence of 0.1 g of 10percent Pd/C overnight at room temperature. The solvent was removed by evaporation an the residue was dissoved in 12 ml of dimethylformamide. 2-chlor-5-nitrobenzoic acid (1.2 g; 6 mMol), 1.7 g of K2CO3, 0.18 g of copper powder and 0.18 g of CuCI were added and the mixture was refluxed for 3 hours. After cooling to room temperature, 12 ml of concentrated HCI and 120 ml of water were added, and the product was extracted with 120 of ethylacetate. The organic phase was dried over Na2SO4 and evaporated. The product was dissolved in 12 ml of methanol; 0.1 g of palladium (10percent ob charcoal) was added and hydrogenated in a hydrogen atmosphere overnight at room temperature. The catalyst was removed by centrifugation, and the solvant was evaporated to obtain compound 1 D.
	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;	Example 4: Chemical synthesis of compounds 89, 93, and 96Nitrophloroglucinol (1 g, 6.5 mMol) was dissolved in 10 ml of methanol and hydrogenated in a hydrogen atmosphere in the presence of 0.1 g of 10percent Pd/C overnight at room temperature. The solvent was removed by evaporation and the residue was dissoved in 12 ml of dimethylformamide. 2-chlor-5-nitrobenzoic acid (1.2 g; 6 mMol), 1.7 g of K2CO3, 0.18 g of copper powder and 0.18 g of CuCI were added and the mixture was refluxed for 3 hours. After cooling to room temperature, 12 ml of concentrated HCI and 120 ml of water were added, and the product was extracted with 120 of ethylacetate. The organic phase was dried over Na2SO4 and evaporated. The product was dissolved in 12 ml of methanol, 0.1 g of palladium (10percent ob charcoal) was added and hydrogenated in an H2-atmosphere overnight at room temperature. The catalyst was removed by centrifugation, and the solvant was evaporated to obtain compound 89.Compound 89 (2 mMol ) was dissolved in 3 ml of methanol at 00C and 0.6 ml of 10 M NaOH and 0.5 mul of fluorbenzoylchlohd (4.2 mMol) was added. After 2.5 hours another portion of 1 ml of 10 M NaOH was added. After 30 min at room temperature, the mixture was acidified with concentrated hydrochloric acid, diluted with 30 ml of water and extracted with 20 ml of ethylacetate. The organic layer was dried and evaporated to obtain compound 93.For reductive amination, compound 89 (1.33 mMol) was dissolved in 2 ml of methanol and 200 mul of cinnamon aldehyde (1.5 mMol) was added. NaBH4 was added in 0.5 mM portions (19 mg each) every 3 hours, until the reaction was complete. The mixture was diluted with water, acidified and extracted with ether. The ether phase was dried, evaporated and compound 96 was obtained.

References: [1]Chemische Berichte,1910,vol. 43,p. 1243.
[2]Patent: WO2010/66912,2010,A2 .Location in patent: Page/Page column 30.
[3]Patent: WO2010/66909,2010,A2 .Location in patent: Page/Page column 41-42.
[4]Journal of Cellular Biochemistry,2012,vol. 113,p. 156 - 164.

5
[ 63458-87-7 ]
[ 16600-92-3 ]

References: [1]Chemische Berichte,1908,vol. 41,p. 4175.

6
[ 16600-92-3 ]
[ 77-78-1 ]
[ 14227-18-0 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 6818 - 6825.
[2]Journal of Organic Chemistry,1954,vol. 19,p. 1359.

7
[ 67-56-1 ]
[ 108-73-6 ]
[ 16600-92-3 ]
[ 16600-93-4 ]
[ 16600-95-6 ]
[ 109482-55-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 1184 - 1185.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 1184 - 1185.

8
[ 108-73-6 ]
[ 16600-92-3 ]
[ 16600-93-4 ]
[ 16600-95-6 ]
[ 109482-55-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 1184 - 1185.

9
[ 480-66-0 ]
[ 16600-92-3 ]

References: [1]Monatshefte fur Chemie,1982,vol. 113,p. 73 - 80.

10
[ 16600-92-3 ]
[ 108-24-7 ]
[ 16740-76-4 ]

References: [1]Monatshefte fur Chemie,1982,vol. 113,p. 73 - 80.

11
[ 16600-92-3 ]
[ 108-24-7 ]
[ 81325-88-4 ]

References: [1]Monatshefte fur Chemie,1982,vol. 113,p. 73 - 80.

12
[ 108-73-6 ]
[ 64-19-7 ]
[ 16600-92-3 ]
[ 16600-93-4 ]
[ 16600-95-6 ]
[ 109482-55-5 ]

13
[ 108-73-6 ]
[ 7697-37-2 ]
[ 16600-92-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1861,vol. 119,p. 201.

16
concentrated phloroglucinol [ No CAS ]
[ 16600-92-3 ]

References: [1]Archiv der Pharmazie,1914,vol. 252,p. 173.

17
locanic acid [ No CAS ]
[ 16600-92-3 ]

References: [1]Archiv der Pharmazie,1914,vol. 252,p. 173.

18
[ 7647-01-0 ]
[ 16600-92-3 ]
zinc [ No CAS ]
[ 139173-32-3 ]

References: [1]Chemische Berichte,1910,vol. 43,p. 1243.

19
[ 63458-87-7 ]
potash [ No CAS ]
[ 16600-92-3 ]

References: [1]Chemische Berichte,1908,vol. 41,p. 4175.

20
[ 10135-18-9 ]
[ 16600-92-3 ]

References: [1]Chemische Berichte,1908,vol. 41,p. 4175.

21
[ 16600-92-3 ]
[ 54998-28-6 ]
[ 440122-62-3 ]