CAS 63-91-2|CAS 150-30-1|L-2-Amino-3-phenylpropanoic acid|L-phenylalanine|L-Phenylalanine|(2S)-2-amino-3-phenylpropanoic acid|D-Phenylalanine|L-2-Amino-3-phenyl propionic acid|(S)-alpha-Amino-beta-p...

General Information

Structure

Molecular Formula

C₉H₁₁NO₂

Molecular Mass

165.18914

Exact Mass

165.0789786

Charge

0

InChI

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1

InChIKey

COLNVLDHVKWLRT-QMMMGPOBSA-N

Canonic Smiles

N[C@H](C(=O)O)Cc1ccccc1

Isomeric Smiles

OC(=O)[C@@H](N)Cc1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

-1.19

LogD (pH = 5.5)

-1.18

Log P

-1.18

Rotatable Bonds

3

H Donor

2

H Acceptors

3

Lipinski's Rule of Five

true

Acid pKa

2.47

Polar Surface Area

63.32

Polarizability

17.13

Molar Refractivity

45.12

LOG S

-1.37

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

L-2-Amino-3-phenylpropanoic acidL-PhenylalanineD-PhenylalanineL-2-Amino-3-phenyl propionic acid(S)-alpha-Amino-beta-phenylpropionic acidL-PHENYLALANINE, U.S.P.(S)-2-Amino-3-phenylpropionic acid(S)-2-氨基-3-苯丙酸L-PhenylalanineL-苯基丙氨酸Phenylalanine2-Amino-3-phenylpropanoic acid(2S)-2-Amino-3-phenylpropanoic Acid(S)-α-Amino-benzenepropanoic Acid(S)-α-Aminohydrocinnamic Acid(S)-α-Amino-β-phenylpropionic Acid(S)-(-)-PhenylalanineH-Phe-OHL-PhenylalaninePHENYLALANINEPhe(S)-alpha-Amino-beta-phenylpropionic acid3-phenyl-L-alanineL-phenylalanineF(S)-2-Amino-3-phenylpropionic acidbeta-phenyl-L-alanine

IUPAC Traditional name

L-phenylalanine

IUPAC name

(2S)-2-amino-3-phenylpropanoic acid

Names and Identifiers

Registration numbers

PubChem SID

2489897124901797248982744650570816096347024887247248986578144203

Beilstein Number

1910408

MDL Number

MFCD00064227MFCD00004270

CAS Number

63-91-2150-30-1

EC Number

200-568-1

Council of Europe Number

Flavis Number

FEMA ID

PubChem CID

KEGG ID

Chemspider ID

Wikipedia Title

CHEMBL

CHEBI ID

58095CHEBI:44885CHEBI:17295CHEBI:21370CHEBI:45079CHEBI:44851CHEBI:6282CHEBI:13151

Unique Ingredient Identifier

8P946UF12S

DrugBank ID

DB00120

Merck Index

147271

BRENDA Ligand Database

460625195229559145037203104145949234617101717101823420439721689429

MetaboLights Database

MTBLS873MTBLS3056MTBLS1906MTBLS7MTBLS2336MTBLS1693MTBLS1145MTBLS1757MTBLS881MTBLS742MTBLS4820MTBLS424MTBLS2825MTBLS1935MTBLS816

PubMed Citation Links

2120378724966042220813862473351722112574244642172220921822494897177848581689317513945318219565392383601522143120

Protein Data Bank

1zef3e0n4k3l2iid5nzk6ztm7c4n7oex4cxg4uc55d047aq91amu1kfl1xqw4cxh

SABIO-RK Database

81547031057312436143991243711624812411620575410681069973410719826

UniProt Database

P30880O70324Q76B45B1P1D9B1P1E3P22897Q9WVK4O64963Q92195P85743P85792P85665P34179Q9NDE8Q7WNZ3

BKMS React Database

3972145037519523461459494291710181977701689203171017

MetaCyc Database

PHE

KNApSAcK Database

C00001386

SureChEMBL Database

SCHEMBL8119SCHEMBL23141074

CompTox Database

DTXSID4040763

ACToR Database

10549-09-4

Reaxys Registry

1910408

Golm Database

6c94ea9d-2336-42a3-8319-1ee3002dd0775fa3ce59-6240-453b-81da-10e2152ebd28a7dfaefc-6255-41ed-bcf2-9bbf3a587c7c49b133a6-2eca-40e9-8e71-8d63017e042533455c18-9868-4bbb-b74e-601989015ba509e01e16-229e-47c3-b2e3-e0c9227e52e691a756b1-17a0-4eab-9aeb-9df384b56cb34db9eb04-f9bd-440e-95d6-4a5cb2935bcfa90c4325-50ed-4a68-91d5-bf7471a1fb077b3b0d99-64b1-4ad2-b529-d23fefc71bf24bc25526-d8d7-4014-97b2-926514338de864c0ea34-2449-43e8-baaa-bd950d48d385c07ab7c7-8f5e-48ba-bb66-d6689bb0e248ffab4215-b149-4fde-bb24-55b27606f7fabc16fa18-9f6f-4500-b7a7-9caf3a3bb77a3bbc353f-ff3c-4033-8b28-b616684e8c8e4f0080f3-0afa-4d75-a120-271cd646ccaa

VirtualMetabolicHuman Database

phe_L

Patent number

EP1568283US2007197430US2007202058US2008242593US2002013490US2006223760WO2005010160US2005276870US2004034080EP1657249US2007213260WO2006014429US2004101523US2006189689

BioModels Database

BIOMD0000000470BIOMD0000000469BIOMD0000000473BIOMD0000000472BIOMD0000000497BIOMD0000000496BIOMD0000000471BIOMD0000001061

EnzymePortal Database

Q58054Q9WYH8P0A9J8

Drug Central Database

YMDB Database

KEGG DRUG Database

PDBeChem Database

ECMDB Database

BindingDB Database

Gmelin ID

HMDB Database

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... CA1(759), CA14(23632), CA2(760), CA4(762), CA5A(763), CA7(766)

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00120

Drug Groups

approved; nutraceutical

Description

An essential aromatic amino acid that is a precursor of melanin; dopamine; noradrenalin (norepinephrine), and thyroxine. [PubChem]

Indication

L-phenylalanine may be helpful in some with depression. It may also be useful in the treatment of vitiligo. There is some evidence that L-phenylalanine may exacerbate tardive dyskinesia in some schizophrenic patients and in some who have used neuroleptic drugs.

Pharmacology

Used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; keeps you awake and alert; reduces hunger pains; functions as an antidepressant and helps improve memory.

Toxicity

L-phenylalanine will exacerbate symptoms of phenylketonuria if used by phenylketonurics. L-phenylalanine was reported to exacerbate tardive dyskinesia when used by some with schizophrenia.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver.

Absorption

Absorbed from the small intestine by a sodium dependent active transport process.

External Links

• [Wikipedia]

• [PDRhealth]

MP Biomedicals

02102623

Crystalline
Purity: >99%

02194723

Cell Culture Reagent
Purity: >99%

02199540

White powder.

05220616

MP Biomedicals Rare Chemical collection

Wikipedia

Phenylalanine

Sigma Aldrich

W358509

Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in fiber drum

P5482

Packaging
10 mg in autosmp vl

40541

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

P2126

Packaging
1 kg in poly bottle
100, 500 g in poly bottle

P8740

Packaging
Manufactured and Packaged under cGMP

78019

Other Notes
Growth requirement of various microorganisms1.

TRC

P319415

L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further converted into dopamine, norepinephrine, and epinephrine. L

ChEBI

CHEBI:17295

The L-enantiomer of phenylalanine.

Molecule Details

References

PubChem Literature

From Data Sources

• Hollunger, G. et al.: Acta Pharmacol. Toxicol., 34, 391 (1974)

• Bagchi, S.P. et al.: Biochem. Pharmacol., 26, 900 (1974)

• Formation of the N,N-dibenzyl benzyl ester by reaction with benzyl bromide and base, followed by LAH reduction and Swern oxidation, lead to the N,N-dibenzyl (S)-ɑ-amino aldehyde, a useful chiral intermediate: Org. Synth., 76, 110 (1998).

• Other amino acids have been resolved by crystallization of their complexes with L-phenylalanine, and decomplexation with activated carbon: Chem. Lett., 113 (1984).

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:7