L-Phenylalanine (BioCAD00000013107)

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Metabolite Card

Chinese Name: L-苯丙氨酸
Formula: C9H11NO2 (165.079)
SMILES: 

N[C@@H](CC1=CC=CC=C1)C(O)=O

Synonyms [en]

L-phenylalanine; phenylalanine; (S)-alpha-Amino-beta-phenylpropionic acid; 3-Phenyl-L-alanine; (2S)-2-amino-3-phenylpropanoic acid; phe

Reviewed

Last reviewed on 2026-04-16.

Cite this Page

L-Phenylalanine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/L-Phenylalanine (retrieved 2026-08-20) (CAD Registry RN: BioCAD00000013107). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Phenylalanine (Phe), also known as L-phenylalanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-phenylalanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Phenylalanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aromatic, non-polar amino acid. In humans, phenylalanine 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 (a methyl ester of the aspartic acid/phenylalanine dipeptide). 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).

Cytoplasm Extracellular Mitochondria
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 150-30-1
  • CAS Registry Number: 30394-07-1
  • CAS Registry Number: 63-91-2
  • CAS Registry Number: 67675-33-6
  • PubChem: 3379
  • PubChem: 6140
  • PubChem: 6925665
  • PubChem: 994
  • ChEBI: ChEBI:17295
  • ChEBI: ChEBI:28044
  • ChEBI: ChEBI:58095
  • HMDB: HMDB0000159
  • HMDB: HMDB00159
  • KEGG: C00079
  • BioCyc: PHE
  • NCBI MeSH: Phenylalanine
  • Wikipedia: Phenylalanine
  • DrugBank: DB00120
  • RefMet: RM0135897
  • MoNA: CCMSLIB00000577901
  • MoNA: CCMSLIB00000578130
  • MoNA: CCMSLIB00003142421
  • MoNA: EMBL-MCF_spec102013
  • MoNA: EMBL-MCF_spec352576
  • MoNA: EMBL-MCF_spec352586
  • MoNA: EMBL-MCF_spec98214
  • MoNA: GLS00057
  • MoNA: HMDB0000159_c_ms_1252
  • MoNA: HMDB0000159_c_ms_1304
  • MoNA: HMDB0000159_ms_ms_248
  • MoNA: HMDB0000159_ms_ms_249
  • MoNA: HMDB0000159_ms_ms_250
  • MoNA: KNA00089
  • MoNA: KNA00090
  • MoNA: KNA00091
  • MoNA: KNA00092
  • MoNA: KNA00384
  • MoNA: KNA00385
  • MoNA: KNA00386
  • MoNA: KNA00387
  • MoNA: KNA00760
  • MoNA: KNA00761
  • MoNA: KO001563
  • MoNA: KO001564
  • MoNA: KO001565
  • MoNA: KO001566
  • MoNA: KO001567
  • MoNA: KO003666
  • MoNA: KO003667
  • MoNA: KO003668
  • MoNA: KO003669
  • MoNA: KO003670
  • MoNA: KZ000052
  • MoNA: MoNA003341
  • MoNA: MoNA003342
  • MoNA: MoNA003343
  • MoNA: MoNA003344
  • MoNA: MoNA003345
  • MoNA: MoNA003346
  • MoNA: MoNA010327
  • MoNA: MoNA010328
  • MoNA: MoNA010329
  • MoNA: MoNA010330
  • MoNA: MoNA010331
  • MoNA: MoNA010332
  • MoNA: MoNA033662
  • MoNA: MoNA033664
  • MoNA: MoNA033665
  • MoNA: MoNA033666
  • MoNA: MoNA033667
  • MoNA: MoNA033669
  • MoNA: MoNA035817
  • MoNA: MoNA035818
  • MoNA: MoNA035819
  • MoNA: MoNA037016
  • MoNA: MoNA037017
  • MoNA: MoNA037018
  • MoNA: MoNA037708
  • MoNA: MoNA037711
  • MoNA: MoNA038457
  • MoNA: MoNA038904
  • MoNA: MT000018
  • MoNA: OUF00320
  • MoNA: OUF01009
  • MoNA: PB000407
  • MoNA: PB000408
  • MoNA: PB000409
  • MoNA: PM000939
  • MoNA: PM000990
  • MoNA: PR010036
  • MoNA: PR030014
  • MoNA: PR100031
  • MoNA: PR100032
  • MoNA: PR100497
  • MoNA: PS005401
  • MoNA: PS005402
  • MoNA: PS005403
  • MoNA: PS005404
  • MoNA: PS005405
  • MoNA: PS005406
  • MoNA: RP000401
  • MoNA: RP000402
  • MoNA: RP000403
  • MoNA: RP000411
  • MoNA: RP000412
  • MoNA: UA005501
  • Metlin: METLIN_28
  • Coconut NaturalProduct: CNP0193965.1
  • Coconut NaturalProduct: CNP0556712.0
  • PMHub: MS000000008
  • metaboanalyst: 0118947b8c749508867901ea6252a768
  • metaboanalyst: 21d0b9cf6faef222ac503e6599a3d5a3
  • metaboanalyst: 3a2a45bc7778edca11d24307e642744f
  • metaboanalyst: 79c2d9c7cc5cbf6702508f11587076d1
  • HERB: HBIN033585
  • HERB: HBIN039503

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00686 5.1.1.11 L-phenylalanine racemase (ATP-hydrolysing)
KEGG:R00688 1.4.1.20 L-phenylalanine:NAD+ oxidoreductase (deaminating)
KEGG:R00689 1.4.3.2 L-phenylalanine:oxygen oxidoreductase (deaminating)
KEGG:R00690 1.13.12.9 L-phenylalanine:oxygen 2-oxidoreductase (decarboxylating)
KEGG:R00691 4.2.1.51 L-arogenate hydro-lyase (decarboxylating; L-phenylalanine-forming)
KEGG:R00692 2.6.1.58 L-phenylalanine:pyruvate aminotransferase
KEGG:R00693 2.3.1.53 acetyl-CoA:L-phenylalanine N-acetyltransferase
KEGG:R00694 2.6.1.1 L-phenylalanine:2-oxoglutarate aminotransferase
KEGG:R00695 2.6.1.70 L-aspartate:phenylpyruvate aminotransferase
KEGG:R00697 4.3.1.24 L-phenylalanine ammonia-lyase (trans-cinnamate-forming)
KEGG:R00698 1.11.1.21 L-phenylalanine:oxygen oxidoreductase (decarboxylating)
KEGG:R00699 4.1.1.28 L-phenylalanine carboxy-lyase (phenylethylamine-forming)
KEGG:R01375 2.6.1.64 L-glutamine:phenylpyruvate aminotransferase
KEGG:R01376 2.6.1.28 L-tryptophan:phenylpyruvate aminotransferase
KEGG:R01795 1.14.16.1 L-phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase (4-hydroxylating)
KEGG:R03660 6.1.1.20 L-phenylalanine:tRNA(Ala) ligase (AMP-forming)
KEGG:R06744 C00079<=>C01456
KEGG:R07211 1.14.16.1 L-phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase(4-hydroxylating)
KEGG:R08463 C00079<=>C08301
KEGG:R08652 1.14.14.40 L-phenylalanine,NADPH:oxygen oxidoreductase (N-hydroxylating, decarboxylating)
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Mass Spectrum
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View All Mass Spectrum
Organism Source

Taxonomy Source

  1. Aconitum variegatum [ncbi taxid: 112594]
  2. Allium sativum [ncbi taxid: 4682]
  3. Aniba megaphylla [ncbi taxid: ]
  4. Arabidopsis thaliana [ncbi taxid: 3702]
  5. Areca catechu [ncbi taxid: 184783]
  6. Berberis integerrima [ncbi taxid: 1112794]
  7. Brassica juncea [ncbi taxid: 3707]
  8. Brassica oleracea var. sabauda [ncbi taxid: 1216010]
  9. Calvatia fenzlii [ncbi taxid: 626502]
  10. Calvatia gigantea [ncbi taxid: 68762]
  11. Calvatia lilacina [ncbi taxid: 2979578]
  12. Canarium villosum [ncbi taxid: ]
  13. Catharanthus roseus [ncbi taxid: 4058]
  14. Centipeda minima [ncbi taxid: 397370]
  15. Cestrum nocturnum [ncbi taxid: 225615]
  16. Cheilanthes fragrans [ncbi taxid: ]
  17. Chlamydomonas reinhardtii [ncbi taxid: 3055]
  18. Cichorium endivia [ncbi taxid: 114280]
  19. Cineraria aspera [ncbi taxid: 240646]
  20. Cistanche deserticola [ncbi taxid: 161395]
  21. Clerodendrum calamitosum [ncbi taxid: 2571307]
  22. Codonopsis pilosula [ncbi taxid: 86864]
  23. Codonopsis pilosula subsp. tangshen [ncbi taxid: 94284]
  24. Codonopsis pilosula var. modesta [ncbi taxid: 94283]
  25. Codonopsis subglobosa [ncbi taxid: 1392605]
  26. Codonopsis tangshen [ncbi taxid: ]
  27. Colla carapacis [ncbi taxid: ]
  28. Colla carapacis et plastri testudinis [ncbi taxid: ]
  29. Concha meretricis seu cyclinae [ncbi taxid: ]
  30. Cornu saigae tataricae [ncbi taxid: ]
  31. Cucumis sativus [ncbi taxid: 3659]
  32. Daucus carota [ncbi taxid: 4039]
  33. Echinopsis macrogona [ncbi taxid: ]
  34. Elephantopus angustifolius [ncbi taxid: ]
  35. Escherichia coli [ncbi taxid: 562]
  36. Escherichia coli K12 [ncbi taxid: ]
  37. Fadogia agrestis [ncbi taxid: ]
  38. Fagopyrum esculentum [ncbi taxid: 3617]
  39. Ficus simplicissima [ncbi taxid: 1822162]
  40. FOOD SAKE [ncbi taxid: ]
  41. Ginkgo biloba [ncbi taxid: 3311]
  42. Grevillea robusta [ncbi taxid: 105748]
  43. Herbertus sakuraii [ncbi taxid: 280633]
  44. Homo sapiens [ncbi taxid: 9606]
  45. Isoplexis sceptrum [ncbi taxid: ]
  46. Libocedrus decurrens [ncbi taxid: ]
  47. Loranthus parasiticus [ncbi taxid: ]
  48. Lycium barbarum [ncbi taxid: 112863]
  49. Lycopersicon esculentum [ncbi taxid: ]
  50. Lycopersicon esculentum var.cerasiforme (DUNAL) ALEF. [ncbi taxid: ]
  51. Mentha canadensis [ncbi taxid: 294733]
  52. Mus musculus [ncbi taxid: 10090]
  53. Nauclea latifolia [ncbi taxid: ]
  54. Ostrya carpinifolia [ncbi taxid: 176865]
  55. Ovibos moschatus [ncbi taxid: 37176]
  56. Pinellia ternata [ncbi taxid: 199225]
  57. Pisum sativum [ncbi taxid: ]
  58. Plastrum testudinis [ncbi taxid: ]
  59. Plastrum testudinis praparata [ncbi taxid: ]
  60. Rehmannia glutinosa [ncbi taxid: 99300]
  61. Rhodospirillum rubrum [ncbi taxid: 1085]
  62. Saccharomyces cerevisiae [ncbi taxid: 4932]
  63. Salvia hispanica [ncbi taxid: 49212]
  64. Sclerotium poriae cocos [ncbi taxid: ]
  65. Semen astragali complanati [ncbi taxid: ]
  66. Semen juglandis [ncbi taxid: ]
  67. Semen sojae praeparata [ncbi taxid: ]
  68. Sinapis alba [ncbi taxid: 3728]
  69. Sinocrassula indica [ncbi taxid: 91157]
  70. Stephania dielsiana [ncbi taxid: 1501458]
  71. Taraxacum borealisinense [ncbi taxid: ]
  72. Taraxacum coreanum [ncbi taxid: 1041103]
  73. Taraxacum formosanum [ncbi taxid: 170733]
  74. Taraxacum mongolicum [ncbi taxid: 90037]
  75. Taraxacum officinale [ncbi taxid: 50225]
  76. Taraxacum platycarpum [ncbi taxid: 170727]
  77. Ulva lactuca [ncbi taxid: 63410]
  78. Ziziphus jujuba [ncbi taxid: 326968]
  79. Zyzzya fuliginosa [ncbi taxid: 1346156]

Pathway Synthetic

pathway id name
BioCyc:LEISH_PWY3IU-255 biopterin metabolism
BioCyc:LEISH_TRNA-CHARGING-PWY tRNA charging pathway
BioCyc:LEISH_PWY3IU-746 phenylalanine degradation
BioCyc:TRYPANO_ANAPHENOXI-PWY phenylalanine degradation II (anaerobic)
PathBank:SMP0000808 Inner Membrane Transport
PathBank:SMP0000820 tRNA Charging
PathBank:SMP0000824 tRNA Charging 2
PathBank:SMP0000827 Phenylalanine Biosynthesis
PathBank:SMP0000938 Phenylalanine Metabolism
WikiPathways:WP513 Catecholamine synthesis
WikiPathways:WP194 Phenylalanine biosynthesis
WikiPathways:WP522 Biogenic amine synthesis
WikiPathways:WP3604 Biochemical pathways: part I
WikiPathways:WP1538 Flavonoid biosynthesis
WikiPathways:WP3622 AtMetExpress overview
WikiPathways:WP154 Biogenic amine synthesis
WikiPathways:WP662 Amino acid metabolism
WikiPathways:WP661 Glucose homeostasis
WikiPathways:WP4598 Glucosinolate biosynthesis (from aromatic amino acid)
WikiPathways:WP125 Biogenic amine synthesis
View All Pathways