Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-10-07 20:38:48 UTC |
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NP-MRD ID | NP0001493 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | N-Acetyl-L-phenylalanine |
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Description | N-Acetyl-L-phenylalanine or N-Acetylphenylalanine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-phenylalanine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-phenylalanine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-phenylalanine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylphenylalanine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free phenylalanine can also occur. In particular, N-Acetyl-L-phenylalanine can be biosynthesized from L-phenylalanine and acetyl-CoA by the enzyme phenylalanine N-acetyltransferase (EC 2.3.1.53). N-Acetyl-L-phenylalanine is a potential uremic toxin and is considered as a hazardous amphipathic metabolite of phenylalanine (PMID: 4038506 ). Many N-acetylamino acids, including N-acetylphenylalanine, are classified as uremic toxins (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-Acetyl-L-phenylalanine appears in large amount in urine of patients with phenylketonuria (PKU), which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine (PMID: 3473611 ). N-Acetyl-L-phenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] Which is found in the phenylalanine metabolism pathway. N-Acetyl-L-phenylalanine is produced for medical, feed, and nutritional applications such as in the preparation of aspartame. Afalanine (N-Acetyl-DL-phenylalanine) is also approved for use as an antidepressant. |
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Structure | CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1 |
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Synonyms | Value | Source |
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Acetyl-L-phenylalanine | ChEBI | Acetylphenylalanine | ChEBI | L-N-Acetylphenylalanine | ChEBI | N-Acetylphenylalanine | ChEBI | N-Acetyl-3-phenyl-L-alanine | HMDB | N-Acetyl-L-phenalanine | HMDB | N-Acetylphenylalanine, (D,L)-isomer, 3H-labeled | HMDB | N-Acetylphenylalanine, (L)-isomer | HMDB | N-Acetylphenylalanine, (L)-isomer, 3H-labeled | HMDB | N-Acetylphenylalanine, (D)-isomer | HMDB |
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Chemical Formula | C11H13NO3 |
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Average Mass | 207.2258 Da |
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Monoisotopic Mass | 207.08954 Da |
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IUPAC Name | (2S)-2-acetamido-3-phenylpropanoic acid |
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Traditional Name | acetyl-L-phenylalanine |
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CAS Registry Number | 2018-61-3 |
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SMILES | CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1 |
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InChI Key | CBQJSKKFNMDLON-JTQLQIEISA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Phenylalanine and derivatives |
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Alternative Parents | |
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Substituents | - Phenylalanine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- 3-phenylpropanoic-acid
- Amphetamine or derivatives
- Monocyclic benzene moiety
- Benzenoid
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 171 - 173 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 6450 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | 0.93 | Green, P. G., Hinz, R. S., Cullander, C., Yamane, G., & Guy, R. H. (1991). Lontophoretic delivery of amino acids and amino acid derivatives across the skin in vitro. Pharmaceutical research, 8(9), 1113-1120. |
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Predicted Properties | |
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General References | - Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
- Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. [PubMed:12013218 ]
- Mach H, Middaugh CR, Lewis RV: Detection of proteins and phenol in DNA samples with second-derivative absorption spectroscopy. Anal Biochem. 1992 Jan;200(1):20-6. [PubMed:1375815 ]
- Okajima K, Inoue M, Morino Y: Studies on the mechanism for renal elimination of N-acetylphenylalanine: its pathophysiologic significance in phenylketonuria. J Lab Clin Med. 1985 Jan;105(1):132-8. [PubMed:4038506 ]
- Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
- Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
- Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
- Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
- Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
- Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]
- Jellum E, Horn L, Thoresen O, Kvittingen EA, Stokke O: Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolism. Scand J Clin Lab Invest Suppl. 1986;184:21-6. [PubMed:3473611 ]
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