2-Amino-2-methyl-3-phenylpropanoic acid [C10H13NO2]

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Date

1 substances in Reaxys

2018-03-20 14h:30m:50s (EST)

O

1. Query HO H 2N

Search as: As drawn AND (IDE.XRN=2803960)

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Reaxys ID 2803960 View in Reaxys

1/1 CAS Registry Number: 1132-26-9 Chemical Name: 2-methyl-3-phenylalanine; alpha-methylphenylalanine; 2-amino-3-phenyl-2-methylpropanoic acid; α-methylphenylalaninne; α-Methylphenylalanine; 2-amino-2-methyl-3phenyl-propionic acid; 2-Amino-2-methyl-3-phenyl-propionsaeure Linear Structure Formula: C10H13NO2 Molecular Formula: C10H13NO2 Molecular Weight: 179.219 Type of Substance: isocyclic InChI Key: HYOWVAAEQCNGLE-UHFFFAOYSA-N Note:

O HO

H 2N

Substance Label (6) Label References 14

Lacivita, Enza; Kwizera, Chantal; Perrone, Roberto; Lucente, Ermelinda; Antunes, Ines F.; Colabufo, Nicola A.; Niso, Mauro; Elsinga, Philip H.; Leopoldo, Marcello; De Giorgio, Paola; Bioorganic and Medicinal Chemistry; vol. 25; nb. 1; (2017); p. 277 - 292, View in Reaxys

α-methyl-Phe

Remelli, Maurizio; Faccini, Stefania; Conato, Chiara; Chirality; vol. 26; nb. 6; (2014); p. 313 - 318, View in Reaxys

3c

Wang, Boyuan; Zhang, Wei; Zhang, Leilei; Du, Da-Ming; Liu, Gang; Xu, Jiaxi; European Journal of Organic Chemistry; nb. 2; (2008); p. 350 - 355, View in Reaxys

7+BnBr

Belokon', Yuri N.; Bhave, Devayani; D'Addario, Daniela; Groaz, Elizabetta; Maleev, Viktor; North, Michael; Pertrosyan, Armine; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2045 - 2048, View in Reaxys

α-Me-Phe

Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; Larionov, Oleg V.; Singh, Ishwar; Parmar, Virinder S.; Vyskocil, Stepan; Kagan, Henri B.; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 7041 - 7048, View in Reaxys

DL-43

Chenault, H. Keith; Dahmer, Juergen; Whitesides, George M.; Journal of the American Chemical Society; vol. 111; nb. 16; (1989); p. 6354 - 6364, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound prophetic product

Patent; VERENIUM CORPORATION; US2011/27346; (2011); (A1) English, View in Reaxys; Patent; Weiner, David P.; Varvak, Alexander; Richardson, Toby; Podar, Mircea; Burke, Ellen; Healey, Shaun; US2012/177722; (2012); (A1) English, View in Reaxys Claim

Patent; Imperial Chemical Industries PLC; US4474767; (1984); (A1) English, View in Reaxys; Patent; The Rockefeller University; US5817628; (1998); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

-1.269

H Bond Donors

2

H Bond Acceptors

3

Rotatable Bonds

3

TPSA

63.32

Lipinski Number

4

Veber Number

2

Related Structure (1) References Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys Derivative (5) Comment (Derivative)

References

Hydrochlorid. F: Patent; Merck and Co.; Inc.; US3758559; (1973); Chem.Abstr.; vol. 79; nb. 146849, View in Reaxys 241-244 grad; UV

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HCl: Bollinger; Journal of medicinal chemistry; vol. 14; nb. 4; (1971); p. 373 - 375, View in Reaxys C10H13NO2*HCl: aus gleichen Teilen der enantiomeren Basen u. wss. Salzsaeure; F: 241-244grad, UV-Max. (Me.): 252.5 nm, 258 nm u. 264 nm Hydrochlorid: F: 214grad; <α>(589)20: -8.6grad (c=1, H2O)

Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys

Hydrochlorid: F: 240-245grad <Zers.>

Cohen; Lo; Journal of Biological Chemistry; vol. 245; (1970); p. 5718,5724, View in Reaxys

Hydrochlorid Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143, View in Reaxys C10H13NO2*HCl: Zers.-Pkt.: 234.5-241grad (aus 95percentig. wss. A.+Ae.); sintert bei ca.

220grad; IR-Banden; NMR-Sp. Melting Point (6) 1 of 6

Melting Point [°C]

230

Comment (Melting Point)

with Sublimation

Kuebel,B. et al.; Chemische Berichte; vol. 112; (1979); p. 128 - 137, View in Reaxys 2 of 6

Melting Point [°C]

275 - 276

Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys 3 of 6

Melting Point [°C]

318

Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys 4 of 6

Melting Point [°C]

275 - 276

Solvent (Melting Point)

aq. ethanol

Jean; Anatol; Bulletin de la Societe chimique de France; vol. 10; (1970); p. 3698 - 3703, View in Reaxys 5 of 6

Melting Point [°C]

294.5 - 295

Comment (Melting Point)

Decomposition.

Stein et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 700,702, View in Reaxys 6 of 6

Melting Point [°C]

293 - 294

Solvent (Melting Point)

H2O

Comment (Melting Point)

Decomposition.

Herbst; Johnson; Journal of the American Chemical Society; vol. 54; (1932); p. 2463,2467, View in Reaxys Sublimation (1) Comment (Sublimation)

References

>230grad

Patent; BASF AG; FR2237892; (1975); DE2336718; Chem.Abstr.; vol. 82; nb. 156263, View in Reaxys

Further Information (4) Description (Fur- References ther Information)

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Further information

Patent; Merck and Co.; Inc.; US3758559; (1973); Chem.Abstr.; vol. 79; nb. 146849, View in Reaxys

Further information

Bollinger; Journal of medicinal chemistry; vol. 14; nb. 4; (1971); p. 373 - 375, View in Reaxys

Further information

Lee et al.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2540,2544, View in Reaxys

Further information

Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-4.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys NMR Spectroscopy (7) 1 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- D2O scopy) Liu, Weiguo; Ray, Paul; Benezra, Steven A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1995); p. 553 - 560, View in Reaxys 2 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 3 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 4 of 7

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

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Liu, Weiguo; Ray, Paul; Benezra, Steven A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1995); p. 553 - 560, View in Reaxys 5 of 7

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)

1H-1H.

Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 6 of 7

Description (NMR Spec- NMR with shift reagents troscopy) Hulst; De Vries; Feringa; Journal of Organic Chemistry; vol. 59; nb. 24; (1994); p. 7453 - 7458, View in Reaxys

7 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Kuebel,B. et al.; Chemische Berichte; vol. 112; (1979); p. 128 - 137, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Jean; Anatol; Bulletin de la Societe chimique de France; vol. 10; (1970); p. 3698 - 3703, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Delvalle et al.; Biochemical Journal; vol. 170; (1978); p. 449,451, View in Reaxys

Medchem (4) 1 of 4

Target Name

Phenylalanine-4-hydroxylase [Rattus norvegicus]

Target Synonyms

pah; phe-4-monooxygenase; phenylalanine-4-hydroxylase

Target Uniprot ID

p04176

Target PDB ID

1phz; 2phm

Target, Subunit, Species Phenylalanine-4-hydroxylase [Rattus norvegicus] Target Mutant/Chimera Details

Phenylalanine-4-hydroxylase [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Ratio of substrate to that of compound to give less than 50 inhibition of rat liver phenylalanine hydroxylase; 1/1 upon incubation in 10 umoles of sodium phosphate, pH 7.4 for 20 minutes at 37 degree C

Biological Species/NCBI Rattus norvegicus ID

2 of 4

Substance RN

2803960View in Reaxys

Measurement Parameter

Ratio

Qualitative value

ND

Target Name

Tyrosine 3-monooxygenase [taurine cattle]

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Target Synonyms

th; tyrosine 3-hydroxylase; tyrosine 3-monooxygenase

Target Uniprot ID

p17289

Target, Subunit, Species Tyrosine 3-monooxygenase [taurine cattle] Target Mutant/Chimera Details

Tyrosine 3-monooxygenase [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of Tyrosine hydroxylase at a concentration of 1E-4 M using unfortified (without addition of reduced pteridine cofactor) beef adrenal medulla tissue

Biological Species/NCBI taurine cattle ID

3 of 4

Substance RN

2803960View in Reaxys

Substance Dose

= 0.0001 M

Measurement Parameter

% Inhibition

Unit

%

Qualitative value

=

Quantitative value

86

Measurement pX

4.79

Target Name

General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae]

Target Synonyms

general amino-acid permease gap1

Target, Subunit, Species General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae] Target Mutant/Chimera Details

General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae]:Wild

Target Species (Bioactivity)

Saccharomyces cerevisiae

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of [14C] L-citrulline (1 mM ) transport in nitrogen-starved Saccharomyces cerevisiae by General amino acid permease (Gap1) upon incubation with compound using short term assay

Biological Species/NCBI Saccharomyces cerevisiae ID

4 of 4

Substance RN

2803960View in Reaxys

Qualitative Results

No inhibition

Measurement Parameter

Activity

Unit

%

Measurement Object

Inhibition

Qualitative value

<

Quantitative value

15

Target Name

Pyridoxal Phosphate [Rattus norvegicus]

Target Synonyms

pyridoxal phosphate

Target, Subunit, Species Pyridoxal Phosphate [Rattus norvegicus] Target Mutant/Chimera Details

Pyridoxal Phosphate [Rattus norvegicus]:Wild

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Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Affinity constant was evaluated for rat Pyridoxal phosphate (0.1 mM) by ''deltaA method''

Biological Species/NCBI Rattus norvegicus ID Substance RN

2803960View in Reaxys

Qualitative Results

1/Kd not calculated

Measurement Parameter

Qualitative

Measurement Object

1/Kd

Concomitants: Compound name

Pyridoxal phosphate

Concomitants: Compound role

SUB

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