Showing metabocard for L-Phenylalanine (MMDBc0000048)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:28:29 UTC
Update Date2024-09-27 22:45:41 UTC
Metabolite IDMMDBc0000048
Metabolite Identification
Common NameL-Phenylalanine
DescriptionPhenylalanine is an essential amino acid and the precursor of the amino acid tyrosine. Like tyrosine, phenylalanine is also a precursor for catecholamines including tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in a number of high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. As a general rule, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylketonurics have elevated serum plasma levels of phenylalanine up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004 ). Phenylalanine has been found to interfere with different cerebral enzyme systems. Untreated phenylketonuria (PKU) can lead to intellectual disability, seizures, behavioural problems, and mental disorders. It may also result in a musty smell and lighter skin. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with phenylketonuria. Mild phenylketonuria can act as an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimer's disease and Parkinson's disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200 ). Phenylalanine also has some potential benefits. Phenylalanine can act as an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For instance, some tumours use more phenylalanine than others (particularly melatonin-producing tumours called melanomas).
Structure
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Synonyms
ValueSource
(S)-2-Amino-3-phenylpropionic acidChEBI
(S)-alpha-Amino-beta-phenylpropionic acidChEBI
3-Phenyl-L-alanineChEBI
beta-Phenyl-L-alanineChEBI
FChEBI
PheChEBI
PHENYLALANINEChEBI
(S)-2-Amino-3-phenylpropionateGenerator
(S)-a-Amino-b-phenylpropionateGenerator
(S)-a-Amino-b-phenylpropionic acidGenerator
(S)-alpha-Amino-beta-phenylpropionateGenerator
(S)-Α-amino-β-phenylpropionateGenerator
(S)-Α-amino-β-phenylpropionic acidGenerator
b-Phenyl-L-alanineGenerator
Β-phenyl-L-alanineGenerator
(-)-beta-PhenylalanineHMDB
(L)-PhenylalanineHMDB
(S)-(-)-PhenylalanineHMDB
(S)-2-Amino-3-phenylpropanoateHMDB
(S)-2-Amino-3-phenylpropanoic acidHMDB
(S)-alpha-Amino-benzenepropanoateHMDB
(S)-alpha-Amino-benzenepropanoic acidHMDB
(S)-alpha-AminobenzenepropanoateHMDB
(S)-alpha-Aminobenzenepropanoic acidHMDB
(S)-alpha-AminohydrocinnamateHMDB
(S)-alpha-Aminohydrocinnamic acidHMDB
(S)-PhenylalanineHMDB
alpha-AminohydrocinnamateHMDB
alpha-Aminohydrocinnamic acidHMDB
beta-Phenyl-alpha-alanineHMDB
beta-PhenylalanineHMDB
L-2-Amino-3-phenylpropionateHMDB
L-2-Amino-3-phenylpropionic acidHMDB
Phenyl-alanineHMDB
PhenylalamineHMDB
L-Isomer phenylalanineHMDB
Phenylalanine, L isomerHMDB
Phenylalanine, L-isomerHMDB
EndorphenylHMDB
(6S)-TetrahydrofolateHMDB
(6S)-Tetrahydrofolic acidHMDB
(6S)-THFAHMDB
5,6,7,8-TetrahydrofolateHMDB
TetrahydrofolateHMDB
THFHMDB
5,6,7,8-Tetrahydrofolic acidHMDB
Molecular FormulaC9H11NO2
Average Mass165.1891
Monoisotopic Mass165.078978601
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number63-91-2
SMILESNot Available
InChI Identifier
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
InChI KeyCOLNVLDHVKWLRT-QMMMGPOBSA-N