Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:20 UTC |
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Update date | 2019-11-26 03:07:30 UTC |
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Primary ID | FDB012739 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Serine |
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Description | L-Serine, also known as 3-hydroxyalanine or serin, belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, L-serine is considered to be a fatty acid lipid molecule. L-Serine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Serine is found, on average, in the highest concentration within a few different foods, such as caseins, red bell peppers, and milk (cow) and in a lower concentration in yellow wax beans, butternut squash, and swiss chards. L-Serine has also been detected, but not quantified in, several different foods, such as cascade huckleberries, rocket salad (ssp.), alaska wild rhubarbs, climbing beans, and liquorices. This could make L-serine a potential biomarker for the consumption of these foods. |
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CAS Number | 56-45-1 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C3H7NO3 |
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IUPAC name | 2-amino-3-hydroxypropanoic acid |
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InChI Identifier | InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7) |
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InChI Key | MTCFGRXMJLQNBG-UHFFFAOYSA-N |
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Isomeric SMILES | NC(CO)C(O)=O |
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Average Molecular Weight | 105.0926 |
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Monoisotopic Molecular Weight | 105.042593095 |
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Classification |
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Description | Belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine 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 | Serine and derivatives |
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Alternative Parents | |
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Substituents | - Serine or derivatives
- Alpha-amino acid
- Beta-hydroxy acid
- Hydroxy acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Alcohol
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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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 | C 34.29%; H 6.71%; N 13.33%; O 45.67% | DFC |
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Melting Point | Mp 228° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 425 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -3.07 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 9.34 (15°, 0.2M KNO3) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -69.5 (5M HCl) | DFC |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0200-9000000000-dc5e2afcfab602641180 | 2014-09-20 | View Spectrum | GC-MS | L-Serine, 2 TMS, GC-MS Spectrum | splash10-0159-1900000000-8e5f1894ee1cb3b7e3d9 | Spectrum | GC-MS | L-Serine, 4 TMS, GC-MS Spectrum | splash10-03di-0930000000-4dc3077a90bf3daff5c4 | Spectrum | GC-MS | L-Serine, non-derivatized, GC-MS Spectrum | splash10-0uxr-0960000000-72799edaa81cd10dc486 | Spectrum | GC-MS | L-Serine, non-derivatized, GC-MS Spectrum | splash10-0159-0900000000-edb7de63d68f317dc1dd | Spectrum | Predicted GC-MS | L-Serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06sl-9000000000-23b7ff74f306e229e4ed | Spectrum | Predicted GC-MS | L-Serine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0089-9810000000-06fed7f6e260b107d95a | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0a4i-4900000000-3f93120669caa8042e73 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-9100000000-0f9a39d1f5d7189dbec0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-9000000000-948720369b4759232b19 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03dl-9000000000-ab6a722fc111a67e6756 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0900000000-20e689eb5cc63e11bd01 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0bti-9600000000-bc82bffef1dd9c4787b6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03dr-9000000000-f19f7b54ca6e6b6f90e1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4r-9700000000-18d2c402d240f6209b00 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-9000000000-32aad5ff017e576a3cbe | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4r-9820000000-329e157e11708de1c960 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-06ri-9320000000-7aeaceb154912fab6e7c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03ds-9030000000-07bab791f412b5ef2968 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03ds-9120000000-81fcc8f743b2c1472458 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0900000000-3d77f3228dc2e322f724 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0bti-9700000000-71eff48f7fa6167dfe43 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-9210000000-452ed7772dfc17d1f8b4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0bti-9500000000-03adc989c5c319caa262 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03ds-9040000000-d0ca4931687f595af73d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0900000000-288773e12a924c5d1047 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06ri-9200000000-d1e0851b72d8c23ee443 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-9000000000-4372abe1326c63681ba5 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-0d30b75120d259484b02 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-8900000000-a5181e1e27d9d858893e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fe0-9200000000-dd033f8c8aa0e218a707 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0abc-9000000000-c4cee4145392d8715828 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 22.5 MHz, D2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 5736 |
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ChEMBL ID | CHEMBL11298 |
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KEGG Compound ID | C00065 |
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Pubchem Compound ID | 5951 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17115 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00133 |
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HMDB ID | HMDB00187 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCP29-I:HKL05-W |
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EAFUS ID | 3390 |
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Dr. Duke ID | SERINE |
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BIGG ID | 33717 |
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KNApSAcK ID | C00001393 |
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HET ID | SER |
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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 | L-Serine |
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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 | |
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Enzymes | Name | Gene Name | UniProt ID |
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Serine hydroxymethyltransferase, mitochondrial | SHMT2 | P34897 | Serine hydroxymethyltransferase, cytosolic | SHMT1 | P34896 | Serine palmitoyltransferase 1 | SPTLC1 | O15269 | Phosphatidylserine synthase 1 | PTDSS1 | P48651 | Phosphatidylserine synthase 2 | PTDSS2 | Q9BVG9 | L-serine dehydratase/L-threonine deaminase | SDS | P20132 | Serine dehydratase-like | SDSL | Q96GA7 | Serine racemase | SRR | Q9GZT4 | Serine--tRNA ligase, mitochondrial | SARS2 | Q9NP81 | Serine--tRNA ligase, cytoplasmic | SARS | P49591 | Serine palmitoyltransferase 2 | SPTLC2 | O15270 | Serine palmitoyltransferase 3 | SPTLC3 | Q9NUV7 |
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Pathways | |
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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 | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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