Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:08:16 UTC |
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Update date | 2015-10-09 22:30:08 UTC |
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Primary ID | FDB022084 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | N-Acetyl-L-phenylalanine |
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Description | Acetylphenylalanine is a hazardous amphipathic metabolite of phenylalanine. It appears in large amount in urine of patients with phenylketonuria which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine. Acetylphenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] in the pathway phenylalanine metabolism. (KEGG; Wikipedia) [HMDB] |
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CAS Number | 2018-61-3 |
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Structure | |
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Synonyms | Synonym | 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 | N-acetyl-3-phenyl-L-Alanine | hmdb | N-Acetyl-l-phenalanine | hmdb | N-Acetyl-L-phenylalanine | hmdb |
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Predicted Properties | |
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Chemical Formula | C11H13NO3 |
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IUPAC name | (2S)-2-acetamido-3-phenylpropanoic acid |
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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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Isomeric SMILES | CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O |
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Average Molecular Weight | 207.2258 |
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Monoisotopic Molecular Weight | 207.089543287 |
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Classification |
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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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Ontology |
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Disposition | Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | N-Acetyl-L-phenylalanine, 2 TMS, GC-MS Spectrum | splash10-00kf-3980000000-205dc96635b498baa46c | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, 1 TMS, GC-MS Spectrum | splash10-00dl-3920000000-50af7cdc34df34b89e91 | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum | splash10-00kf-3980000000-205dc96635b498baa46c | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum | splash10-00dl-3920000000-50af7cdc34df34b89e91 | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum | splash10-0fr7-1950000000-8c9c63efeb473bcf7625 | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum | splash10-00dl-2920000000-f0ce2160cf1eb9d38d56 | Spectrum | GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum | splash10-0f6x-2910000000-33afe725162942dc296a | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9400000000-2c91eb9a78faef00e1da | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dl-9110000000-e910d5b4824d2e88d697 | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | N-Acetyl-L-phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-0900000000-9e69c187ac8560365826 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-0900000000-04559809a9c6261f18b6 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ufr-5900000000-a8bb0fc573e6143527aa | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0a4i-0090000000-2dcdf0ed503251026e40 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-2920000000-7447f1e30d868cae5af6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0lxy-8900000000-3b53da8f8106adfdd677 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0pbc-9400000000-1737db9a05bf29f3701a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4l-9100000000-f015dd2066ebbefec15a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0a4l-1960000000-20faf15c3d02bbe80ad2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-0900000000-891ecddb54dab32f4dce | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-1900000000-6867cba730dee8712265 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-2900000000-2e77f5a51bec17ed674e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0udi-4900000000-c9aadc8231b14121aa8c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-02tc-0900000000-ac3b438665d0b035a7e2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-00di-0900000000-a426a7fbff06e9213f59 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-00di-0900000000-0d8dd7876525745785ff | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0fdo-6900000000-ad4d31f8b5e3e0474416 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0090000000-2dcdf0ed503251026e40 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-2920000000-7447f1e30d868cae5af6 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0btc-2950000000-2865ae294df6193f5a75 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-044l-2900000000-1b1f3d364775a1619b26 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-9bb5ea6eb4c3ab49ee32 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-2890000000-293238d6264d01ab86c4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0900-5910000000-b912a04d31d0b03a8552 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9200000000-1b69d466f84616cfe628 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 67404 |
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ChEMBL ID | CHEMBL55743 |
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KEGG Compound ID | C03519 |
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Pubchem Compound ID | 74839 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16259 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00512 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Glycine N-acyltransferase | GLYAT | Q6IB77 | Glycine N-acyltransferase-like protein 1 | GLYATL1 | Q969I3 | Glycine N-acyltransferase-like protein 2 | GLYATL2 | Q8WU03 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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