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Chemical Structure| 6419-36-9 Chemical Structure| 6419-36-9
Chemical Structure| 6419-36-9

*Storage: Inert atmosphere,Room Temperature.

3-Pyridylacetic acid HCl

CAS No.: 6419-36-9

3-Pyridylacetic acid HCl is a homolog of nicotinic acid, a degradation product of nicotine and other tobacco alkaloids, used in medicinal chemistry for studying anti-inflammatory and neuroprotective effects.

Synonyms: 3-Pyridylacetic acid hydrochloride

4.5 *For Research Use Only !

Cat. No.: A172627 Purity: 95%

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Product Details of [ 6419-36-9 ]

CAS No. :6419-36-9
Formula : C7H8ClNO2
M.W : 173.60
SMILES Code : O=C(O)CC1=CC=CN=C1.[H]Cl
Synonyms :
3-Pyridylacetic acid hydrochloride
MDL No. :MFCD00012819
InChI Key :XVCCOEWNFXXUEV-UHFFFAOYSA-N
Pubchem ID :2723724

Safety of [ 6419-36-9 ]

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

Calculated chemistry of [ 6419-36-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 42.75
TPSA ?

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

50.19 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

0.74
Log Po/w (WLOGP)?

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

1.51
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.

0.39
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

1.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.74

Water Solubility

Log S (ESOL):?

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

-1.65
Solubility 3.85 mg/ml ; 0.0222 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.

-1.37
Solubility 7.35 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 (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.77
Solubility 2.93 mg/ml ; 0.0169 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

Yes
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.

-6.83 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

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)

1.41

Application In Synthesis [ 6419-36-9 ]

* 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 [ 6419-36-9 ]

[ 6419-36-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 6419-36-9 ]
  • [ 39998-25-9 ]
YieldReaction ConditionsOperation in experiment
98% With sulfuric acid; for 1h;Reflux; To a solution of 2-(pyri din-3 -yl)acetic acid hydrochloride (17.3 g, 100 mmol, 1 equiv) in MeOH (80 mL) was added concentrated H2SO4 (6.4 mL, 120 mmol, 1.2 equiv) dropwise at room temperature and the resulting mixture was refluxed for 1 hour. The reaction mixture was poured into saturated NaHC03 solution and extracted with DCM (3 *100 mL). The combined organic phase were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo to afford the title compound methyl 2-(pyridin-3-yl)acetate as yellow solid (15 g, 98% yield). LC-MS: m/z 152.1 (M+H)+
97% In order to synthesize 3-pyridylethanethiol, 3-pyridylethanol as an intermediate therefor was synthesized by the following method. Into a 1-L flask to which a nitrogen gas introduction tube, thermometer, Dimroth condenser, and dropping funnel had been attached was introduced 25.12 g (0.145 mol) of 3-pyridylacetic acid monohydrochloride. Thereto was added 500 mL of anhydrous methanol. After the atmosphere in the flask was replaced with nitrogen, the contents were stirred at room temperature to dissolve the monohydrochloride. Thereto was added dropwise 31.12 g (0.248 mol) of thionyl chloride. Thereafter, the resultant mixture was heated and reacted for further 2.5 hours with refluxing. After the reaction, the reaction mixture was cooled to room temperature, and the methanol was distilled off under vacuum. The residue was neutralized with a saturated aqueous solution of sodium hydrogen carbonate. An extraction operation using 100 mL of ethyl acetate was conducted three times, and anhydrous sodium sulfate was added to the resultant organic phase to dry the phase. The anhydrous sodium sulfate was removed by decantation. Thereafter, the solvent was distilled off under vacuum. Thus, 21.29 g (0.141 mol) of methyl 3-pyridylacetate, which is the methanol ester of 3-pyridylacetic acid, was obtained (yield, 97%).
  • 2
  • [ 6419-36-9 ]
  • [ 4771-49-7 ]
  • [ 1316694-93-5 ]
  • 3
  • [ 6419-36-9 ]
  • [ 19690-13-2 ]
 

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