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Chemical Structure| 19883-77-3 Chemical Structure| 19883-77-3
Chemical Structure| 19883-77-3

H-Phe(3-F)-OH

CAS No.: 19883-77-3

4.5 *For Research Use Only !

Cat. No.: A327766 Purity: 98%

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Product Details of [ 19883-77-3 ]

CAS No. :19883-77-3
Formula : C9H10FNO2
M.W : 183.18
SMILES Code : [H][C@](N)(CC1=CC=CC(F)=C1)C(O)=O
MDL No. :MFCD00066450
InChI Key :VWHRYODZTDMVSS-QMMMGPOBSA-N
Pubchem ID :716315

Safety of [ 19883-77-3 ]

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

Calculated chemistry of [ 19883-77-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 45.46
TPSA ?

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

63.32 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.31
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

-1.89
Log Po/w (WLOGP)?

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

1.2
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.

-0.69
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

1.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.24

Water Solubility

Log S (ESOL):?

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

0.07
Solubility 216.0 mg/ml ; 1.18 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

1.08
Solubility 2200.0 mg/ml ; 12.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-2.15
Solubility 1.31 mg/ml ; 0.00716 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.

-8.76 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

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)

1.86

Application In Synthesis of [ 19883-77-3 ]

* 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 [ 19883-77-3 ]

[ 19883-77-3 ] Synthesis Path-Downstream   1~29

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  • [ 58632-95-4 ]
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  • [ 114873-01-7 ]
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  • C34H30FN3O3(2-)*Ni(2+) [ No CAS ]
  • [ 19883-77-3 ]
  • 6
  • [ 24424-99-5 ]
  • [ 19883-77-3 ]
  • [ 114873-01-7 ]
YieldReaction ConditionsOperation in experiment
100% A mixture of L-2-AMINO-3- (3-FLUORO- phenyl)-propionic acid (20.0 g, 110 MMOL, 1 eq) in H20 (100 mL) was treated with NA2CO3 (16.2 g, 153 mmol, 1.4 eq) in H20 (40 mL) followed by 1,4-dioxane (100 mL) and cooled to 0 C. The BOZO was added and the reaction mixture was stirred at ambient temperature for 5 h after which the- dioxane was evaporated. H2O (125 mL) was then added and the mixture then washed with Et2O (2 x 100 mL). The aqueous phase was acidified with 10% citric acid followed by extraction with EtOAc (2 x 300 mL). The combined EtOAc layers were washed with H20 (2 x 150 mL), brine (150 mL), dried (Na2SO4) and concentrated to give the acid as a colorless, viscous oil which slowly solidified upon standing (31 G, QUANT). H NMR (CDC13) 7.33-7. 26 (m, 1H), 7.00-6. 91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J=14, 5.3, 2H), 1. 44 (s, 9H) ; Anal CALCD for C14HL8NO4F : C, 59.36 ; H, 6.40 ; N, 4.94. Found: C, 59.29 ; H, 6.34 ; N, 4.90.
100% With sodium carbonate; In 1,4-dioxane; water; at 0 - 25℃; for 5h; A mixture of BOC-L-3-fluorophenylalanine 1 (20 g, 109 MMOL) in water was treated with sodium carbonate (16.2 g, 15.3 MMOL) in H20 (40 mL). 1,4-Dioxane (100 mL) was added, and the mixture cooled to 0 C. The BOC20 (28. 6 g, 120 MMOL) was added in one portion, and the mixture was maintained for 5 h at 25 C. The solvent was evaporated and H2O (125 mL) was added. The aqueous layer was washed with diethyl ether (2 x 100 mL). The ether layers were discarded, and the aqueous layer was acidified with a 10% citric acid solution. The mixture was then extracted with EtOAc (2 x 150 mL). The organic layers were combined, washed with H20 (2 x 150 mL), Brine (150 mL), dried (NA2SO4), filtered and evaporated to give the desire crude product 2 as a clear viscous oil. 30.9 9, 100%, ) which slowly solidified to a white solid at rt. 1H NMR (300 MHz, CDCl3) 8 7.33-7. 26 (M, 1H), 7.00-6. 91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J= 14,5. 3 Hz, 2H), 1.44 (s, 9H) ppm; Anal CALCD for CR4HR8NO4F : C, 59.36 ; H, 6.40 ; N, 4.94. Found: C, 59.29 ; H, 6.34 ; N, 4.90.
97% With sodium hydrogencarbonate; In tetrahydrofuran; water;pH 9.0; 3-Fluoro-L-Phenylalanine (1 g, 5.46 mmol, Combi-blocks, Cat SS-0819, Lot L78093) was dissolved in THF (15 mL) and water (15 mL) and the pH of the solution was adjusted to 9 using saturated sodium bicarbonate solution. Di -tert- butyl -di carbonate (1.31 g, 6 mmol) was added to the solution slowly and was stirred overnight. After completion of the reaction, the pH of the solution was adjusted to 4 using 0.1 M HC1 and the aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with water (x2) followed by brine, dried using sodium sulfate, filtered and concentrated under reduced pressure to afford 1.5 g (97% yield) off-white solid of the title product (Int-1). LCMS (+ESI) M+H+(-Boc)=l 84.1.
  • 7
  • [ 49759-64-0 ]
  • [ 19883-77-3 ]
  • 8
  • [ 64493-16-9 ]
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  • 9
  • 2-Amino-3-(3-fluoro-phenyl)-propionic acid isobutyl ester; hydrochloride [ No CAS ]
  • [ 19883-77-3 ]
  • 10
  • [ 1866-38-2 ]
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  • 12
  • [ 56-40-6 ]
  • [ 456-41-7 ]
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  • [ 110117-84-5 ]
  • 13
  • [ 67-56-1 ]
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  • methyl (S)-2-amino-3-(3-fluorophenyl)propanoate hydrochloride [ No CAS ]
  • 15
  • [ 19883-77-3 ]
  • (R)-3-amino-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]
  • 17
  • [ 19883-77-3 ]
  • (S)-2-[(S)-1-(3,5-Dichloro-benzenesulfonyl)-pyrrolidine-2-carbonyl]-amino}-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]
  • 18
  • [ 19883-77-3 ]
  • (S)-2-[(S)-1-(3,5-Dichloro-benzenesulfonyl)-pyrrolidine-2-carbonyl]-amino}-3-(3-fluoro-phenyl)-propionic acid methyl ester [ No CAS ]
  • 19
  • [ 19883-77-3 ]
  • (S)-2-[(S)-1-(3,5-Dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]
  • 20
  • [ 19883-77-3 ]
  • (S)-2-[(S)-1-(3,5-Dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-3-(3-fluoro-phenyl)-propionic acid methyl ester [ No CAS ]
  • 21
  • [ 19883-77-3 ]
  • [ 142995-36-6 ]
  • 22
  • [ 19883-77-3 ]
  • (S)-2-Amino-N-benzyl-3-(3-fluoro-phenyl)-N-methyl-propionamide; hydrochloride [ No CAS ]
  • 23
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  • [ 142995-45-7 ]
  • 24
  • [ 19883-77-3 ]
  • <(1-methyl-1H-indol-3-yl)carbonyl>-(2S,4R)Hyp-Phe(3-F)-NMeBzl [ No CAS ]
  • 25
  • [ 19883-77-3 ]
  • (2S,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid [(S)-1-(benzyl-methyl-carbamoyl)-2-(3-fluoro-phenyl)-ethyl]-amide; hydrochloride [ No CAS ]
  • 26
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  • [ 125218-23-7 ]
  • 27
  • [ 380-70-1 ]
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  • 28
  • [ 17607-28-2 ]
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  • 29
  • [ 49759-56-0 ]
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