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phenylalanine

File:L-Phenylalanin_-_L-Phenylalanine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ170545· pop 64· linked from 4,130 articles

phenylalanine

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Also known as L-Phe, (S)-2-Amino-3-phenylpropionic acid, (S)-alpha-Amino-beta-phenylpropionic acid, 3-phenyl-L-alanine, beta-Phenyl-L-alanine, F, Phe, β-phenyl-L-alanine

OverviewAI-generated

Phenylalanine is a chemical compound with the formula C₉H₁₁NO₂. Its IUPAC name is (2S)-2-azaniumyl-3-phenylpropanoate. The substance has a mass of 165.079 and a density of 1.29. It melts at 283 degrees and has a pKa of 9.24.

Chemical properties include an xlogp of -0.9 and a topological polar surface area of 67.8. The molecule features one hydrogen bond donor and two hydrogen bond acceptors, with a net charge of 0.

The compound is associated with the Commons category "L-Phenylalanine". It is referenced by 4,130 other encyclopedia articles.

Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C9H11NO2
Molecular weight
165.19 g/mol
IUPAC name
(2S)-2-azaniumyl-3-phenylpropanoate
SMILES
C1=CC=C(C=C1)C[C@@H](C(=O)[O-])[NH3+]
InChIKey
COLNVLDHVKWLRT-QMMMGPOBSA-N
XLogP
-0.9
Polar surface area
67.8 Ų
H-bond donors
1
H-bond acceptors
2
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 3
Molecule type
Small molecule
Indications
Central Nervous System Neoplasm

via ChEMBL · EBI

Research

106,068 papers

via PubMed

Wikidata facts

Has part
oxygen
Mass
165.079
Has use
medication
Show 12 more facts
Commons category
L-Phenylalanine
found in taxon
Sinorhizobium meliloti
chemical formula
C₉H₁₁NO₂
pKa
9.24
described by source
Armenian Soviet Encyclopedia
World Health Organisation international non-proprietary name
phenylalanine
canonical SMILES
C1=CC=C(C=C1)CC(C(=O)O)N
melting point
283
density
1.29
isomeric SMILES
N[C@@H](CC1=CC=CC=C1)C(O)=O
NCI Thesaurus ID
C29601
has characteristic
bitterness
Sources (4)

via Wikidata · CC0

~10 min read

Encyclopedic overview

13 sections
Contents
  • History
  • Dietary sources
  • Dietary recommendations
  • Other biological roles
  • In plants
  • Biosynthesis
  • Phenylketonuria
  • <small>D</small>-, <small>L</small>- and <small>DL</small>-phenylalanine
  • Commercial synthesis
  • Derivatives
  • See also
  • References
  • External links

thumb|Phenylalanine ball and stick model spinning Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the biological pigment melanin. It is encoded by the messenger RNA codons UUU and UUC.

Phenylalanine is found naturally in the milk of mammals. It is used in the manufacture of food and drink products and sold as a nutritional supplement as it is a direct precursor to the neuromodulator phenethylamine. As an essential amino acid, phenylalanine is not synthesized de novo in humans and other animals, who must ingest phenylalanine or phenylalanine-containing proteins.

Excerpted from Wikipedia’s “phenylalanine” article, available under the CC BY-SA 4.0 licence.

Gallery (10)

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