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L-phenylalanine (CHEBI:17295)

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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:13151, CHEBI:21370, CHEBI:6282, CHEBI:45079, CHEBI:44851, CHEBI:44885
Supplier Information
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Formula Source
C9H11NO2 KEGG COMPOUND
Net Charge 0
Average Mass 165.18918
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 Source
Isolated from Homo sapiens (NCBI:9606) DOI
Roles Classification
Chemical Role(s): 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.
micronutrient

Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
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 on the 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 micronutrient (CHEBI:27027)
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 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)-2-cyano-1-(4-phenyl-L-phenylalanyl)pyrrolidine (CHEBI:43666) has functional parent L-phenylalanine (CHEBI:17295)
(2S,3S)-β-methylphenylalanine (CHEBI:77031) has functional parent L-phenylalanine (CHEBI:17295)
3-chloro-L-phenylalanine (CHEBI:49597) has functional parent L-phenylalanine (CHEBI:17295)
4-fluoro-L-phenylalanine (CHEBI:44909) has functional parent L-phenylalanine (CHEBI:17295)
4-fluorophenyl-L-alanine (CHEBI:10625) has functional parent L-phenylalanine (CHEBI:17295)
m-fluoro-L-phenylalanine (CHEBI:77957) has functional parent L-phenylalanine (CHEBI:17295)
m-tyrosine (CHEBI:44303) has functional parent L-phenylalanine (CHEBI:17295)
N,N-dihydroxy-L-phenylalanine (CHEBI:47991) has functional parent L-phenylalanine (CHEBI:17295)
N-acyl-L-phenylalanine (CHEBI:77673) has functional parent L-phenylalanine (CHEBI:17295)
N-hydroxy-L-phenylalanine (CHEBI:47990) 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)
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)
bortezomib (CHEBI:52717) has functional parent L-phenylalanine (CHEBI:17295)
Cys-Phe-Phe-Gly (CHEBI:73460) has functional parent L-phenylalanine (CHEBI:17295)
Gln-Phe-Trp-Tyr (CHEBI:73464) 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)
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)
methyl L-phenylalaninate (CHEBI:49339) 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-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-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-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-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-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
Database Links Databases
C00001386 KNApSAcK
C00079 KEGG COMPOUND
D00021 KEGG DRUG
DB00120 DrugBank
ECMDB00159 ECMDB
HMDB00159 HMDB
PHE PDBeChem
PHE MetaCyc
Phenylalanine Wikipedia
YMDB00304 YMDB
View more database links
Registry Numbers Types Sources
1910408 Reaxys Registry Number Reaxys
1910408 Beilstein Registry Number Beilstein
50837 Gmelin Registry Number Gmelin
63-91-2 CAS Registry Number KEGG COMPOUND
63-91-2 CAS Registry Number NIST Chemistry WebBook
63-91-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16893175 PubMed citation CiteXplore
17784858 PubMed citation CiteXplore
21203787 PubMed citation CiteXplore
21956539 PubMed citation CiteXplore
22081386 PubMed citation CiteXplore
22112574 PubMed citation CiteXplore
22143120 PubMed citation CiteXplore
22209218 PubMed citation CiteXplore
22494897 PubMed citation CiteXplore
23836015 PubMed citation CiteXplore
24464217 PubMed citation CiteXplore
24733517 PubMed citation CiteXplore
24966042 PubMed citation CiteXplore
General Comments
2014-07-10 Species Info: Escherichia coli; Tax id: NCBI: 562; Citation: MED:24966042
2014-07-10 Species Info: Saccharomyces cerevisiae; Tax id: NCBI: 4932; Citation: MED:24733517
 
Last Modified
28 August 2014

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