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Chemical Structure| 30563-98-5 Chemical Structure| 30563-98-5

Structure of 30563-98-5

Chemical Structure| 30563-98-5

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Product Details of [ 30563-98-5 ]

CAS No. :30563-98-5
Formula : C8H8N2O4
M.W : 196.16
SMILES Code : O=C(OCC)C1=NC=C([N+]([O-])=O)C=C1
MDL No. :MFCD09751108
InChI Key :PZFHVUFNOKRFEC-UHFFFAOYSA-N
Pubchem ID :45116302

Safety of [ 30563-98-5 ]

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

Computational Chemistry of [ 30563-98-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 4
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 49.15
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

85.01 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.39
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.88
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.17
Log Po/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.

-0.36
Log Po/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

-0.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.7

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.29
Solubility 0.997 mg/ml ; 0.00508 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.

-3.29
Solubility 0.101 mg/ml ; 0.000516 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

-1.89
Solubility 2.52 mg/ml ; 0.0129 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

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

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.

-6.16 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)

2.14

Application In Synthesis of [ 30563-98-5 ]

* 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 [ 30563-98-5 ]

[ 30563-98-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 30651-24-2 ]
  • [ 64-17-5 ]
  • [ 30563-98-5 ]
YieldReaction ConditionsOperation in experiment
95% A solution of <strong>[30651-24-2]5-nitro-pyridine-2-carboxylic acid</strong> (38.0 g, 226 mmol) in thionyl chloride (50.0 ml, 686 mmol) was heated at reflux for 1 h and concentrated to a solid, which was dissolved in anhydrous ethanol (100 mL), refluxed 2 h, and allowed to cool. The solvent was evaporated in vacuo. The resultant solid residue was dissolved in ethyl acetate (500 mL), washed with 1 M aq. sodium bicarbonate (2 x 300 mL), dried over sodium sulfate, and concentrated to give 39.0 g (86percent yield) of a yellow solid, which was more than 95percent pure [BYAPOS;H] NMR and LCMS. 'H NMR [(DMSO-D6)] : [8] 9.46 (d, [1H,] J = 2.1 Hz), 8.76 (dd, [1H,] J = 2.1, 8. 6 Hz), 8.29 (d, [1H,] J [=8. 6HZ),] 4.41 (q, 2H, [J = 7. 1 HZ),] 1.36 (t, 3H, [J = 7. 1 HZ).] LCMS-APCI (M+H+) : 197.
86% A solution of <strong>[30651-24-2]5-nitro-pyridine-2-carboxylic acid</strong> (38.0 g, 226 mmol) in thionyl chloride (50.0 ml, 686 mmol) was heated at reflux for 1 h and concentrated to a solid, which was dissolved in anhydrous ethanol (100 mL), refluxed 2 h, and allowed to cool. The solvent was evaporated in vacuo. The resultant solid residue was dissolved in ethyl acetate (500 mL), washed with 1 M aq. sodium bicarbonate (2*300 mL), dried over sodium sulfate, and concentrated to give 39.0 g (86percent yield) of a yellow solid, which was more than 95percent pure by 1H NMR and LCMS. 1H NMR (DMSO-d6): .box.9.46 (d, 1H, J=2.1 Hz), 8.76 (dd, 1H, J=2.1, 8.6 Hz), 8.29 (d, 1H, J=8.6 Hz), 4.41 (q, 2H, J=7.1 Hz), 1.36 (t, 3H, J=7.1 Hz). LCMS-APCI (M+H+): 197.
A mixture of delta-nitro-pyridine^-carboxylic acid (Step 39.5) (5.74 g, 34.2 mmol), H2SO4 (1 ml.) and EtOH (50 ml.) was stirred for 1.5 h at reflux. The residue was diluted with EtOAc and saturated solution of NaHCO3. The aqueous layer was separated and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and <n="90"/>concentrated to afford 6.1 g of the title compound as a white solid: ES-MS: 197.1 [M+H]+; tR= 3.22 min (System 1 ).
 

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