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:CB5928169, ZINC000060094177
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Triiodothyronine, also known as T3, is a thyroid hormone. It affects almost every physiological process in the body, including growth and development, metabolism, body temperature, and heart rate. Production of T3 and its prohormone thyroxine (T4) is activated by thyroid-stimulating hormone (TSH), which is released from the anterior pituitary gland. This pathway is part of a closed-loop feedback process: Elevated concentrations of T3, and T4 in the blood plasma inhibit the production of TSH in the anterior pituitary gland. As concentrations of these hormones decrease, the anterior pituitary gland increases production of TSH, and by these processes, a feedback control system stabilizes the level of thyroid hormones in the bloodstream. At the cellular level, T3 is the body's more active and potent thyroid hormone. T3 helps deliver oxygen and energy to all of the body's cells, its effects on target tissues being roughly four times more potent than those of T4. Of the thyroid hormone that is produced, just about 20% is T3, whereas 80% is produced as T4. Roughly 85% of the circulating T3 is later formed in the liver and anterior pituitary by removal of the iodine atom from the carbon atom number five of the outer ring of T4. In any case, the concentration of T3 in the human blood plasma is about one-fortieth that of T4. The half-life of T3 is about 2.5 days. The half-life of T4 is about 6.5 days. T3 levels start to rise 45 minutes after administration and peak at about 2.5 hours. Although manufacturer of Cytomel states half-life to be 2.5 days the half-life variability is great and can vary depending on the thyroid status of the patient. Newer studies have found the pharmakokinetics of T3 to be complex and the half-life to vary between 10 – 22 hours.
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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 Types Sources
13945318 PubMed citation Europe PMC
16893175 PubMed citation Europe PMC
17784858 PubMed citation Europe PMC
21203787 PubMed citation Europe PMC
21956539 PubMed citation Europe PMC
22081386 PubMed citation Europe PMC
22112574 PubMed citation Europe PMC
22143120 PubMed citation Europe PMC
22209218 PubMed citation Europe PMC
22494897 PubMed citation Europe PMC
23836015 PubMed citation Europe PMC
24464217 PubMed citation Europe PMC
24733517 PubMed citation Europe PMC
24966042 PubMed citation Europe PMC
Last Modified
06 February 2023