Home Cart Sign in  
Chemical Structure| 949-99-5 Chemical Structure| 949-99-5

Structure of 4-Nitro-L-phenylalanine
CAS No.: 949-99-5

Chemical Structure| 949-99-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 949-99-5 ]

CAS No. :949-99-5
Formula : C9H10N2O4
M.W : 210.19
SMILES Code : N[C@@H](CC1=CC=C([N+]([O-])=O)C=C1)C(O)=O
MDL No. :MFCD00051221
InChI Key :GTVVZTAFGPQSPC-QMMMGPOBSA-N
Pubchem ID :13706

Safety of [ 949-99-5 ]

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

Computational Chemistry of [ 949-99-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 4
Num. H-bond acceptors 5.0
Num. H-bond donors 2.0
Molar Refractivity 54.32
TPSA ?

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

109.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.84
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

-1.25
Log Po/w (WLOGP)?

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

0.55
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.

-2.14
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

-1.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.65

Water Solubility

Log S (ESOL):?

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

-0.39
Solubility 86.1 mg/ml ; 0.41 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.

-0.55
Solubility 59.8 mg/ml ; 0.284 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

-1.25
Solubility 11.7 mg/ml ; 0.0558 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.

-8.47 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

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)

2.03

Application In Synthesis of [ 949-99-5 ]

* 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 [ 949-99-5 ]

[ 949-99-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 949-99-5 ]
  • [ 943-80-6 ]
YieldReaction ConditionsOperation in experiment
87% With barium sulfate; hydrogen; palladium; To a solution of Ap, a mixture of 8 g L-4-nitrophenylalanine (38 mmol) and 0.8 g barium sulfate was put in a 250 mL three-necked flask while adding the gas of hydrogen to do the hydrogenation for 4 h. The reaction mixture was filtered and concentrated to crystallization. The productions were washed with water, dried and evaporated. Finally, we added 5.9 g white powder and the yield was 87%(Fig. 1F) [19].
85% With rosenmund catalyst; hydrogen; In water; at 20℃; for 3h; A mixed solution of concentrated HNO3 (60%) and concentrated H2SO4 (1.4:1.1 v/v) was prepared and chilled to 10 C. Then, a portion of this solution (3.5 mL) was added dropwise under stirring to a solution of L-phenylalanine (4.139 g, 25.1 mmol) in H2SO4 (98%, 12.5 mL). The reaction mixture was stirred at 10 C for 2.5 h. The reaction solution was then adjusted to pH 5 with NH4OH. The pale yellow precipitate formed was collected by filtration, washed with a small volume of water and CH3CN, and then dried to yield 4-nitro-L-phenylalanine as a yellow powder (4.748 g, 90%). 4-Nitro-L-phenylalanine (2.006 g, 9.54 mmol) was suspended in water (35 mL) and subjected tohydrogenation at room temperature for 3 h in the presence of 0.2 g of 5% palladium-barium sulfate.The catalyst was filtered through a Celite pad, and the pale brown filtrate was concentrated. Theresidue was washed with CH3CN to afford a pale brown mass (1.460 g, 85%). No further purificationwas performed for the following step. The 4-amino-L-phenylalanine derivative (0.060 g, 0.33 mmol)was dissolved in 6N HCl (4 mL). Sodium nitrate in water (0.030 g/0.5 mL) was added at 0 C. Thereaction mixture was stirred at the same temperature for 40 min and diluted with 6N HCl (0.25 mL).Subsequently, sodium azide in water (0.033 g/0.75 mL) was added at 0 C. The reaction mixture wasstirred at same temperature for 5 min, and then warmed to room temperature for 1 h, thenconcentrated. The residue was reprecipitated from CH3CN to afford a pure colorless amorphous mass(0.0435 g, 64%). Analytical and spectroscopic data were identical to those reported in the literature [10].
  • 2
  • [ 34404-33-6 ]
  • [ 949-99-5 ]
  • Boc-D-Ala-p-NO2Phe-OH [ No CAS ]
  • 4
  • [ 949-99-5 ]
  • [ 82911-69-1 ]
  • [ 95753-55-2 ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide; In water; acetonitrile; at 20℃; for 3h; A solution of 80 mL of acetonitrile was added to a suspension of 37.7 g (0.179 mol) of acid 2a and 2b in 200 mL of 2% NaOH aqueous solution until complete dissolution. A solution of 61.8 g (0.183 mol) of suspension of Fmoc-OSu in 100 mL of acetonitrile was added to this solution. The reaction mixture was stirred for 3 hours at room temperature and acidified with 5% HCl to pH 4-5. The precipitated white crystals were filtered off, washed with ethyl acetate, and dried. The reaction product was recrystallized from ethanol-dioxane mixture, 50 : 50. Yield 67% (3a), 71% (3b). mp 230C (mp 233-234C [10]). IR spectrum nu, cm-1: 3429, 3202, 1724, 1693, 1601, 1520, 1447, 1354, 1223, 1057, 856, 760, 741. 1 NMR spectrum (DMSO-d6), delta, ppm: 2.90-3.09 m (1H, CH2), 3.25 d.d (1H, CH2, 2J 13.7, 3J 4.3 Hz), 4.13-4.34 m (4H, 2CH2, 2CH), 7.23-7.45 m (4Harom), 7.54 d (2Harom, 3J 8.6 Hz), 7.60-7.64 m (2Harom), 7.79 d (1H, NH, 3J 8.6 Hz), 7.88 d (2Harom, 3J 7.5 Hz ), 8.14 d (2Harom, 3J 8.6 Hz ), 12.93 s (1H, COOH). 13 NMR spectrum (DMSO-d6), delta, ppm: 36.62 (CH2), 47.03 (CH), 55.25 (CH), 66.03 (CH2), 120.56, 123.69, 125.62, 127.45, 128.07, 130.94, 141.16, 144.20, 146.73 (arom), 156.39 (CONH), 173.27 (COOH). Mass spectrum (ESI), m/z: 455.1214 [M + Na]+. C24H20N2O6. Calculated M 432.1321.
 

Historical Records

Categories

Related Functional Groups of
[ 949-99-5 ]

Amino Acid Derivatives

Chemical Structure| 22888-56-8

A120673 [22888-56-8]

2-Amino-3-(3-nitrophenyl)propanoic acid

Similarity: 1.00

Chemical Structure| 444777-67-7

A129971 [444777-67-7]

H-D-Phe(4-NO2)-OH.H2O

Similarity: 1.00

Chemical Structure| 207591-86-4

A132318 [207591-86-4]

(S)-2-Amino-3-(4-nitrophenyl)propanoic acid hydrate

Similarity: 1.00

Chemical Structure| 56613-61-7

A158172 [56613-61-7]

H-D-Phe(4-NO2)-OH

Similarity: 1.00

Chemical Structure| 19883-74-0

A154315 [19883-74-0]

(S)-2-Amino-3-(3-nitrophenyl)propanoic acid

Similarity: 0.98