Phenylalanine
PubChem CID: 6140
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| Compound Synonyms | L-phenylalanine, phenylalanine, 63-91-2, (2S)-2-amino-3-phenylpropanoic acid, (S)-2-Amino-3-phenylpropanoic acid, 3-Phenyl-L-alanine, (S)-Phenylalanine, (L)-Phenylalanine, 3-Phenylalanine, (S)-2-Amino-3-phenylpropionic acid, beta-Phenyl-L-alanine, Antibiotic FN 1636, fenilalanina, H-Phe-OH, L-Alanine, phenyl-, Alanine, 3-phenyl-, L-Antibiotic FN 1636, Phenylalaninum, (S)-alpha-Amino-beta-phenylpropionic acid, L-Alanine, 3-phenyl-, (S)-(-)-Phenylalanine, FEMA No. 3585, Phenylalanine (VAN), beta-Phenylalnine, (-)-, Fenilalanina [Spanish], Phenylalaninum [Latin], (S)-alpha-Aminohydrocinnamic acid, Alanine, phenyl-, L-, endophenyl, (S)-alpha-Amino-benzenepropanoic acid, Phenylalanine, L-, HSDB 1825, Hydrocinnamic acid, alpha-amino-, phe, 2-Amino-3-phenylpropionic acid, L-, NSC 79477, Phenylalamine, Phenylalanine [USAN:INN:JAN], alpha-Aminohydrocinnamic acid, L-, alpha-Amino-beta-phenylpropionic acid, L-, Benzenepropanoic acid, alpha-amino-, (S)-, EINECS 200-568-1, phenylalanin, alpha-Aminohydrocinnamic acid, MFCD00064227, (-)-phenylalanine, L-Phe, laevo-phenyl alanine, UNII-47E5O17Y3R, CCRIS 4254, L-PHENYLALININE, CHEBI:17295, 47E5O17Y3R, (-)-beta-Phenylalanine, NSC-79477, CHEMBL301523, DTXSID4040763, Phenylalanine [USAN:USP:INN:JAN], Phenylalaninum (Latin), PHENYLALANINE (II), PHENYLALANINE [II], 2S-alpha-phenylalanine, PHENYLALANINE (MART.), PHENYLALANINE [MART.], Phenylalanine (L-Phenylalanine), Alanine, phenyl-, PHENYLALANINE (EP MONOGRAPH), PHENYLALANINE [EP MONOGRAPH], Phenylalanine (USAN:USP:INN:JAN), PHENYLALANINE (USP MONOGRAPH), PHENYLALANINE [USP MONOGRAPH], .beta.-Phenylalanine, Phenyl-.alpha.-alanine, L-.beta.-Phenylalanine, .beta.-Phenyl-L-alanine, (-)-.beta.-Phenylalanine, .alpha.-Aminohydrocinnamic acid, .beta.-Phenyl-.alpha.-alanine, Phenylalanine (USP/INN), L-phenylaniline, Hydrocinnamic acid, .alpha.-amino-, 1-phenylalanine, .beta.-Phenyl-.alpha.-alanine, l-, L-phenyl Alanine, PheOH, 1usi, NCI9959, .alpha.-Amino-.beta.-phenylpropionic acid, Phenylalanine1532, racemic phenylalanine, Phenylalanine Phenolic, 1f2p, alpha-Aminohydrocinnamate, L-Phenylalanine, 99%, beta-Phenyl-alpha-alanine, L-Phenylalanine (JP18), PHENYLALANINE [MI], bmse000045, bmse000900, bmse000921, bmse001016, PHENYLALANINE [INN], L-Phenylalanine (Standard), SCHEMBL8119, NCIStruc1_000204, NCIStruc2_000248, PHENYLALANINE [HSDB], PHENYLALANINE [USAN], PHENYLALANINE [VANDF], (S)-alpha-Aminohydrocinnamate, L-Phenylalanine (H-Phe-OH), L-PHENYLALANINE [FCC], L-PHENYLALANINE [JAN], L-2-Amino-3-phenylpropionate, L-PHENYLALANINE [FHFI], L-Phenylalanine, 99%, FCC, PHENYLALANINE [WHO-DD], GTPL3313, (S)-alpha-Aminobenzenepropanoate, DTXCID2020763, (S)-2-amino-3-phenylpropanoate, BDBM18073, HY-N0215R, (S)-2-Amino-3-phenylpropionate, 1F9436B3-8B0D-4AC6-A004-4249B0BDA436, L-PHENYLALANINE [USP-RS], L-Phenylalanine non-animal source, (S)-alpha-Amino-benzenepropanoate, L-2-Amino-3-phenylpropionic acid, 30394-07-1, HY-N0215, L-2-amino-3-phenyl-propionic acid, propanoic acid, 2-amino-3-phenyl-, (S)-alpha-Aminobenzenepropanoic acid, AC8117, CCG-37572, NCGC00013103, L-[2,3,4,5,6-3H]phenylalanine, (S)-alpha-Amino-beta-phenylpropionate, AKOS010373257, AKOS015853585, (S)-.alpha.-Aminobenzenepropanoic acid, DB00120, FP15788, L-Phenylalanine, Vetec(TM), 98.5%, L-Phenylalanine, reagent grade, >=98%, LEUCINE IMPURITY C [EP IMPURITY], NCGC00013103-02, NCGC00013103-03, NCGC00013103-04, NCGC00013103-05, NCGC00095047-01, NCGC00095047-02, NCGC00095047-03, NCGC00095047-04, AC-22417, AS-14129, BP-20538, TYROSINE IMPURITY A [EP IMPURITY], DB-029978, DB-266631, DB-266632, IS_PHENYLALANINE-2,3,4,5,6-D5, L-Phenylalanine, 99%, natural, FCC, FG, NATEGLINIDE IMPURITY D [EP IMPURITY], NS00068215, P0134, Benzenepropanoic acid, .alpha.-amino-, (S)-, EN300-52626, L-Phenylalanine, BioUltra, >=99.0% (NT), C00079, D00021, M02961, L-Phenylalanine, SAJ special grade, >=99.0%, Q170545, L-.ALPHA.-AMINO-.BETA.-PHENYLPROPIONIC ACID, L-Phenylalanine, Vetec(TM) reagent grade, >=98%, L-Phenylalanine, Cell Culture Reagent (H-L-Phe-OH), LYSINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], F0001-2360, Z756430566, L-Phenylalanine, certified reference material, TraceCERT(R), Phenylalanine, European Pharmacopoeia (EP) Reference Standard, L-Phenylalanine, United States Pharmacopeia (USP) Reference Standard, L-Phenylalanine, analytical standard, for Nitrogen Determination According to Kjeldahl Method, L-Phenylalanine, Pharmaceutical Secondary Standard, Certified Reference Material, 200-568-1, L-Phenylalanine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 98.5-101.0% |
|---|---|
| Topological Polar Surface Area | 63.3 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | COLNVLDHVKWLRT-QMMMGPOBSA-N |
| Rotatable Bond Count | 3.0 |
| State | Solid |
| Synonyms | (S)-2-Amino-3-phenylpropionic acid, (S)-alpha-Amino-beta-phenylpropionic acid, 3-Phenyl-L-alanine, beta-Phenyl-L-alanine, F, Phe, PHENYLALANINE, (S)-2-Amino-3-phenylpropionate, (S)-a-Amino-b-phenylpropionate, (S)-a-Amino-b-phenylpropionic acid, (S)-alpha-Amino-beta-phenylpropionate, (S)-Α-amino-β-phenylpropionate, (S)-Α-amino-β-phenylpropionic acid, b-Phenyl-L-alanine, Β-phenyl-L-alanine, (-)-beta-Phenylalanine, (L)-Phenylalanine, (S)-(-)-Phenylalanine, (S)-2-Amino-3-phenylpropanoate, (S)-2-Amino-3-phenylpropanoic acid, (S)-alpha-Amino-benzenepropanoate, (S)-alpha-Amino-benzenepropanoic acid, (S)-alpha-Aminobenzenepropanoate, (S)-alpha-Aminobenzenepropanoic acid, (S)-alpha-Aminohydrocinnamate, (S)-alpha-Aminohydrocinnamic acid, (S)-Phenylalanine, alpha-Aminohydrocinnamate, alpha-Aminohydrocinnamic acid, beta-Phenyl-alpha-alanine, beta-Phenylalanine, L-2-Amino-3-phenylpropionate, L-2-Amino-3-phenylpropionic acid, Phenyl-alanine, Phenylalamine, L-Isomer phenylalanine, Phenylalanine, L isomer, Phenylalanine, L-isomer, Endorphenyl, (6S)-Tetrahydrofolate, (6S)-Tetrahydrofolic acid, (6S)-THFA, 5,6,7,8-Tetrahydrofolate, Tetrahydrofolate, THF, 5,6,7,8-Tetrahydrofolic acid |
| Heavy Atom Count | 12.0 |
| Compound Name | Phenylalanine |
| Kingdom | Organic compounds |
| Description | L-phenylalanine, also known as phe or f, belongs to phenylalanine and derivatives class of compounds. Those are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-phenylalanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-phenylalanine can be found in watermelon, which makes L-phenylalanine a potential biomarker for the consumption of this food product. L-phenylalanine can be found primarily in most biofluids, including sweat, blood, urine, and cerebrospinal fluid (CSF), as well as throughout all human tissues. L-phenylalanine exists in all living species, ranging from bacteria to humans. In humans, L-phenylalanine is involved in a couple of metabolic pathways, which include phenylalanine and tyrosine metabolism and transcription/Translation. L-phenylalanine is also involved in few metabolic disorders, which include phenylketonuria, tyrosinemia type 2 (or richner-hanhart syndrome), and tyrosinemia type 3 (TYRO3). Moreover, L-phenylalanine is found to be associated with viral infection, dengue fever, hypothyroidism, and myocardial infarction. L-phenylalanine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylalanine (Phe or F) is an α-amino acid with the formula C 9H 11NO 2. 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. The codons for L-phenylalanine are UUU and UUC. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the skin pigment melanin . Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver (DrugBank). If PKU is diagnosed early, an affected newborn can grow up with normal brain development, but only by managing and controlling phenylalanine levels through diet, or a combination of diet and medication. The diet requires severely restricting or eliminating foods high in phenylalanine, such as meat, chicken, fish, eggs, nuts, cheese, legumes, milk and other dairy products. Starchy foods, such as potatoes, bread, pasta, and corn, must be monitored. Optimal health ranges (or "target ranges") of serum phenylalanine are between 120 and 360 µmol/L, and aimed to be achieved during at least the first 10 years of life. Recently it has been found that a chiral isomer of L-phenylalanine (called D-phenylalanine) actually arrests the fibril formation by L-phenylalanine and gives rise to flakes. These flakes do not propagate further and prevent amyloid formation by L-phenylalanine. D-phenylalanine may qualify as a therapeutic molecule in phenylketonuria (A8161) (T3DB). |
| Exact Mass | 165.079 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 165.079 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 153.0 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 165.19 |
| Database Name | fooddb_chem_all;hmdb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Uniprot Id | P07101, Q9Y285, O95363, P17735, P20711, P22079, P00439, P30041, P05164, P17174, P00505, P11678, Q16773, Q9NSD9, Q9UHI5, Q8TF71, Q9BYF1, Q96RQ9, Q6IBR2 |
| Defined Atom Stereocenter Count | 1.0 |
| Iupac Name | (2S)-2-amino-3-phenylpropanoic acid |
| Total Atom Stereocenter Count | 1.0 |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Total Bond Stereocenter Count | 0.0 |
| Class | Carboxylic acids and derivatives |
| 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 |
| Smiles | C1=CC=C(C=C1)C[C@@H](C(=O)O)N |
| Xlogp | -1.5 |
| Superclass | Organic acids and derivatives |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Amino acids, peptides, and analogues |
| Taxonomy Direct Parent | Phenylalanine and derivatives |
| Molecular Formula | C9H11NO2 |
- 1. Outgoing r'ship
FOUND_INto/from Citrullus Lanatus (Plant) Rel Props:Source_db:fooddb_chem_all