CHEBI:17295 - L-phenylalanine

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ChEBI Name L-phenylalanine
ChEBI ID CHEBI:17295
ChEBI ASCII Name L-phenylalanine
Definition The L-enantiomer of phenylalanine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45079, CHEBI:44851, CHEBI:44885, CHEBI:6282, CHEBI:13151, CHEBI:21370
Supplier Information ChemicalBook:CB2488691, ChemicalBook:CB51568650, eMolecules:514492, eMolecules:26757996, ZINC000000105196
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Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula C9H11NO2. 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. The one-letter symbol F was assigned to phenylalanine for its phonetic similarity.
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Formula C9H11NO2
Net Charge 0
Average Mass 165.18918
Monoisotopic Mass 165.07898
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
SMILES N[C@@H](Cc1ccccc1)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
EC 3.1.3.1 (alkaline phosphatase) inhibitor
An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of alkaline phosphatase (EC 3.1.3.1).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via phenylalanine )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-phenylalanine (CHEBI:17295) has role Escherichia coli metabolite (CHEBI:76971)
L-phenylalanine (CHEBI:17295) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-phenylalanine (CHEBI:17295) has role algal metabolite (CHEBI:84735)
L-phenylalanine (CHEBI:17295) has role EC 3.1.3.1 (alkaline phosphatase) inhibitor (CHEBI:63332)
L-phenylalanine (CHEBI:17295) has role human xenobiotic metabolite (CHEBI:76967)
L-phenylalanine (CHEBI:17295) has role micronutrient (CHEBI:27027)
L-phenylalanine (CHEBI:17295) has role mouse metabolite (CHEBI:75771)
L-phenylalanine (CHEBI:17295) has role nutraceutical (CHEBI:50733)
L-phenylalanine (CHEBI:17295) has role plant metabolite (CHEBI:76924)
L-phenylalanine (CHEBI:17295) is a L-α-amino acid (CHEBI:15705)
L-phenylalanine (CHEBI:17295) is a erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:73690)
L-phenylalanine (CHEBI:17295) is a phenylalanine (CHEBI:28044)
L-phenylalanine (CHEBI:17295) is a proteinogenic amino acid (CHEBI:83813)
L-phenylalanine (CHEBI:17295) is conjugate acid of L-phenylalaninate (CHEBI:32486)
L-phenylalanine (CHEBI:17295) is conjugate base of L-phenylalaninium (CHEBI:32487)
L-phenylalanine (CHEBI:17295) is enantiomer of D-phenylalanine (CHEBI:16998)
L-phenylalanine (CHEBI:17295) is tautomer of L-phenylalanine zwitterion (CHEBI:58095)
Incoming (2S,3S)-β-methylphenylalanine (CHEBI:77031) has functional parent L-phenylalanine (CHEBI:17295)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) has functional parent L-phenylalanine (CHEBI:17295)
N-phenylacetylphenylalanine (CHEBI:141030) has functional parent L-phenylalanine (CHEBI:17295)
L-Phe-L-Phe-Gly-L-Leu-L-Met-NH2 (CHEBI:191176) has functional parent L-phenylalanine (CHEBI:17295)
L-Phe-Gly-L-Leu-L-Met-NH2 (CHEBI:191175) has functional parent L-phenylalanine (CHEBI:17295)
L-phenylalanine derivative (CHEBI:84144) has functional parent L-phenylalanine (CHEBI:17295)
Ala-Phe-Thr-Ser (CHEBI:73377) has functional parent L-phenylalanine (CHEBI:17295)
Ala-Phe-Trp-Asn (CHEBI:73379) has functional parent L-phenylalanine (CHEBI:17295)
Arg-Phe-Phe-Cys (CHEBI:73402) has functional parent L-phenylalanine (CHEBI:17295)
Asn-Leu-Phe-Asp (CHEBI:73411) has functional parent L-phenylalanine (CHEBI:17295)
Asn-Phe (CHEBI:141424) has functional parent L-phenylalanine (CHEBI:17295)
Asp-Leu-Phe-Val (CHEBI:73431) has functional parent L-phenylalanine (CHEBI:17295)
Asp-Phe-Asp-Gln (CHEBI:73437) has functional parent L-phenylalanine (CHEBI:17295)
Asp-Phe-Val-Tyr (CHEBI:73293) has functional parent L-phenylalanine (CHEBI:17295)
Asp-Phe-Val-Val (CHEBI:73438) has functional parent L-phenylalanine (CHEBI:17295)
Cys-Met-Phe-His (CHEBI:138508) has functional parent L-phenylalanine (CHEBI:17295)
Cys-Phe-Phe-Gly (CHEBI:73460) has functional parent L-phenylalanine (CHEBI:17295)
DON-10-phenylalanine (CHEBI:149457) has functional parent L-phenylalanine (CHEBI:17295)
Gln-Phe (CHEBI:141430) has functional parent L-phenylalanine (CHEBI:17295)
Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-phenylalanine (CHEBI:17295)
Gln-Phe-Tyr (CHEBI:156250) has functional parent L-phenylalanine (CHEBI:17295)
Glu-Gly-Phe (CHEBI:140739) has functional parent L-phenylalanine (CHEBI:17295)
Glu-Ile-Phe (CHEBI:73497) has functional parent L-phenylalanine (CHEBI:17295)
Glu-Leu-Phe-Ala (CHEBI:73485) has functional parent L-phenylalanine (CHEBI:17295)
Glu-Phe-Gln-Gln (CHEBI:73488) has functional parent L-phenylalanine (CHEBI:17295)
Glu-Phe-Val (CHEBI:73501) has functional parent L-phenylalanine (CHEBI:17295)
His-Phe (CHEBI:141438) has functional parent L-phenylalanine (CHEBI:17295)
Leu-enkephalin (CHEBI:89656) has functional parent L-phenylalanine (CHEBI:17295)
Leu-Phe (CHEBI:73585) has functional parent L-phenylalanine (CHEBI:17295)
Leu-Phe-Asn (CHEBI:73570) has functional parent L-phenylalanine (CHEBI:17295)
Leu-Phe-Asp (CHEBI:73571) has functional parent L-phenylalanine (CHEBI:17295)
Lys-Phe (CHEBI:73605) has functional parent L-phenylalanine (CHEBI:17295)
Met-enkephalin (CHEBI:6618) has functional parent L-phenylalanine (CHEBI:17295)
Met-Phe-Met (CHEBI:160990) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Ala (CHEBI:73630) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Ala-Asp (CHEBI:73627) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Ala-Gly (CHEBI:73628) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Ala-Pro (CHEBI:73617) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Arg (CHEBI:73632) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Arg-Thr (CHEBI:144556) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Asn (CHEBI:73633) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Asp (CHEBI:73631) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Asp-Cys (CHEBI:73629) has functional parent L-phenylalanine (CHEBI:17295)
Phe-FMDP (CHEBI:74492) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Gly (CHEBI:73635) has functional parent L-phenylalanine (CHEBI:17295)
Phe-His (CHEBI:73634) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Lys (CHEBI:141443) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Phe (CHEBI:72723) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Phe-Asp (CHEBI:73643) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Pro-Pro (CHEBI:73644) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Pro-Thr (CHEBI:138789) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Ser (CHEBI:71032) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Thr (CHEBI:73636) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Trp-Ala (CHEBI:73640) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Trp-Trp (CHEBI:73642) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Tyr (CHEBI:73637) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Tyr-Asp (CHEBI:84102) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Val (CHEBI:73638) has functional parent L-phenylalanine (CHEBI:17295)
Phe-Val-Asp (CHEBI:73639) has functional parent L-phenylalanine (CHEBI:17295)
Ser-Phe (CHEBI:71029) has functional parent L-phenylalanine (CHEBI:17295)
L-phenylalanine-d5 (CHEBI:192084) is a L-phenylalanine (CHEBI:17295)
L-phenylalaninium (CHEBI:32487) is conjugate acid of L-phenylalanine (CHEBI:17295)
L-phenylalaninate (CHEBI:32486) is conjugate base of L-phenylalanine (CHEBI:17295)
D-phenylalanine (CHEBI:16998) is enantiomer of L-phenylalanine (CHEBI:17295)
L-phenylalanine residue (CHEBI:29997) is substituent group from L-phenylalanine (CHEBI:17295)
L-phenylalanino group (CHEBI:32501) is substituent group from L-phenylalanine (CHEBI:17295)
L-phenylalanyl group (CHEBI:32496) is substituent group from L-phenylalanine (CHEBI:17295)
L-phenylalanine zwitterion (CHEBI:58095) is tautomer of L-phenylalanine (CHEBI:17295)
IUPAC Names
(2S)-2-amino-3-phenylpropanoic acid
L-phenylalanine
Synonyms Sources
(S)-2-Amino-3-phenylpropionic acid HMDB
(S)-alpha-Amino-beta-phenylpropionic acid KEGG COMPOUND
3-phenyl-L-alanine NIST Chemistry WebBook
β-phenyl-L-alanine NIST Chemistry WebBook
F ChEBI
L-Phenylalanine KEGG COMPOUND
Phe ChEBI
PHENYLALANINE PDBeChem
Manual Xrefs Databases
2144 DrugCentral
C00001386 KNApSAcK
C00079 KEGG COMPOUND
D00021 KEGG DRUG
DB00120 DrugBank
ECMDB00159 ECMDB
HMDB0000159 HMDB
PHE PDBeChem
PHE MetaCyc
Phenylalanine Wikipedia
YMDB00304 YMDB
View more database links
Registry Numbers Types Sources
1910408 Reaxys Registry Number Reaxys
50837 Gmelin Registry Number Gmelin
63-91-2 CAS Registry Number KEGG COMPOUND
63-91-2 CAS Registry Number ChemIDplus
63-91-2 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
06 February 2023