Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:11:14 UTC |
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Update date | 2019-11-26 03:21:02 UTC |
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Primary ID | FDB022266 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Phenylacetylglycine |
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Description | Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:
acyl-CoA + glycine < -- > CoA + N-acylglycine
Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292) [HMDB] |
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CAS Number | 500-98-1 |
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Structure | |
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Synonyms | Synonym | Source |
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N-Phenacetylglycine | ChEBI | N-Phenylacetylglycine | ChEBI | Phenaceturic acid | ChEBI | Phenacetylglycine | ChEBI | Phenacetate | Generator | Phenacetic acid | Generator | ((Phenylacetyl)amino)acetic acid | HMDB | N-(Phenylacetyl)-glycine | HMDB | N-(Phenylacetyl)glycine | HMDB | PAA | HMDB | PAG | HMDB | Phenaceturate | HMDB | Phenylacetyl glycine | HMDB | [(Phenylacetyl)amino]acetate | HMDB | [(Phenylacetyl)amino]acetic acid | HMDB | Phenylacetylglycine | MeSH | ((phenylacetyl)amino)acetic acid | hmdb | N-(phenylacetyl)-Glycine | hmdb | phenylacetyl glycine | hmdb |
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Predicted Properties | |
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Chemical Formula | C10H11NO3 |
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IUPAC name | 2-(2-phenylacetamido)acetic acid |
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InChI Identifier | InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14) |
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InChI Key | UTYVDVLMYQPLQB-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)CNC(=O)CC1=CC=CC=C1 |
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Average Molecular Weight | 193.1992 |
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Monoisotopic Molecular Weight | 193.073893223 |
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Classification |
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Description | 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. |
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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 | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Monocyclic benzene moiety
- Benzenoid
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- 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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Physiological effect | Health effect: |
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Disposition | Biological location: Source: |
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Foods | Dairy productsEggsMeats Grains: Nuts and legumes: |
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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 | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-96f6d1819364e0910beb | Spectrum | GC-MS | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0udl-5930000000-6e0622de46a05b80d685 | Spectrum | GC-MS | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0006-9610000000-b8948d031afc0e4b8f78 | Spectrum | GC-MS | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-96f6d1819364e0910beb | Spectrum | GC-MS | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0udl-5930000000-6e0622de46a05b80d685 | Spectrum | GC-MS | Phenylacetylglycine, non-derivatized, GC-MS Spectrum | splash10-0006-9610000000-b8948d031afc0e4b8f78 | Spectrum | Predicted GC-MS | Phenylacetylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9500000000-50b56f103c1a79f65878 | Spectrum | Predicted GC-MS | Phenylacetylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-9200000000-5d39e42ac2b4d7b6f726 | Spectrum | Predicted GC-MS | Phenylacetylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phenylacetylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phenylacetylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phenylacetylglycine, 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) | splash10-004l-9100000000-134ddfbf19f2ee4e9260 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-9656d3b4670efd4db2e3 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-9cf5ff47848cf5bf99b2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-0006-9000000000-f37d59edacbcf679b420 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9200000000-92c7f1e2376eb0e84b36 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-002f-9200000000-c48677787f705755d93f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0006-9300000000-dd5f78904d0d0dacb641 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9300000000-1acb6b8d75e7381ccbde | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0596-9100000000-415a6a1ccc4a5a25ad4f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-002f-9100000000-52063d451d15512ae652 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0006-9000000000-b4cfc8b9dad7406c720f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-002f-9000000000-88eadbe8bb1b30f341b0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-abf76489fbf1b18e56aa | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-00di-9000000000-1168dca79ce76e8ff744 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-709de7804cd48ddac3b5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00di-9000000000-668624127e5eb3cd947a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-f0284ab582fc7a2b28c4 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-9600000000-96499e21a08e5d190040 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00fr-9200000000-aeac60944271030f9751 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00bc-9000000000-4caba04f2e229a8013b4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-899f25422883181dbe57 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006x-4900000000-433c13250fe2463708f4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006x-9200000000-0b6ae74cd7a7ddce62d7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-e21745e55a3af36629b3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-078d0d5a533b72168681 | 2021-09-22 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 61452 |
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ChEMBL ID | CHEMBL458497 |
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KEGG Compound ID | C05598 |
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Pubchem Compound ID | 68144 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 955 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00821 |
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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 | 955 |
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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 | Glycine N-acyltransferase-like protein 3 | GLYATL3 | Q5SZD4 | N-acetyltransferase ESCO1 | ESCO1 | Q5FWF5 |
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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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