| 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 | 2022-02-02 01:00:10 UTC |
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| NP-MRD ID | NP0001084 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | L-Serine |
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| Description | Serine (Ser) or L-serine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-serine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Serine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. In humans, serine is a nonessential amino acid that can be easily derived from glycine. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. L-Serine may be derived from four possible sources: Dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) And, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373 ). |
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| Structure | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])O[H] InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 |
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| Synonyms | | Value | Source |
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| (2S)-2-Amino-3-hydroxypropanoic acid | ChEBI | | (S)-(-)-Serine | ChEBI | | (S)-2-Amino-3-hydroxypropanoic acid | ChEBI | | (S)-alpha-Amino-beta-hydroxypropionic acid | ChEBI | | (S)-Serine | ChEBI | | beta-Hydroxy-L-alanine | ChEBI | | beta-Hydroxyalanine | ChEBI | | L-(-)-Serine | ChEBI | | L-2-Amino-3-hydroxypropionic acid | ChEBI | | L-3-Hydroxy-2-aminopropionic acid | ChEBI | | L-3-Hydroxy-alanine | ChEBI | | L-Ser | ChEBI | | L-Serin | ChEBI | | S | ChEBI | | Ser | ChEBI | | SERINE | ChEBI | | (2S)-2-Amino-3-hydroxypropanoate | Generator | | (S)-2-Amino-3-hydroxypropanoate | Generator | | (S)-a-Amino-b-hydroxypropionate | Generator | | (S)-a-Amino-b-hydroxypropionic acid | Generator | | (S)-alpha-Amino-beta-hydroxypropionate | Generator | | (S)-Α-amino-β-hydroxypropionate | Generator | | (S)-Α-amino-β-hydroxypropionic acid | Generator | | b-Hydroxy-L-alanine | Generator | | Β-hydroxy-L-alanine | Generator | | b-Hydroxyalanine | Generator | | Β-hydroxyalanine | Generator | | L-2-Amino-3-hydroxypropionate | Generator | | L-3-Hydroxy-2-aminopropionate | Generator | | (-)-Serine | HMDB | | (S)-2-Amino-3-hydroxy-propanoate | HMDB | | (S)-2-Amino-3-hydroxy-propanoic acid | HMDB | | (S)-b-Amino-3-hydroxypropionate | HMDB | | (S)-b-Amino-3-hydroxypropionic acid | HMDB | | (S)-beta-Amino-3-hydroxypropionate | HMDB | | (S)-beta-Amino-3-hydroxypropionic acid | HMDB | | 2-Amino-3-hydroxypropanoate | HMDB | | 2-Amino-3-hydroxypropanoic acid | HMDB | | 3-Hydroxy-L-alanine | HMDB | | L Serine | HMDB | | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol | HMDB | | Bo-xan | HMDB | | e 161b | HMDB | | Xanthophyll | HMDB | | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol | HMDB | | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol | HMDB |
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| Chemical Formula | C3H7NO3 |
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| Average Mass | 105.0926 Da |
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| Monoisotopic Mass | 105.04259 Da |
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| IUPAC Name | (2S)-2-amino-3-hydroxypropanoic acid |
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| Traditional Name | L-serine |
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| CAS Registry Number | 56-45-1 |
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| SMILES | N[C@@H](CO)C(O)=O |
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| InChI Identifier | InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 |
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| InChI Key | MTCFGRXMJLQNBG-REOHCLBHSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-03 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2022-02-03 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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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| Species Where Detected | |
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| Chemical Taxonomy |
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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
- L-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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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 228 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 425 mg/mL | Not Available | | LogP | -3.07 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - Kaumeyer JF, Polazzi JO, Kotick MP: The mRNA for a proteinase inhibitor related to the HI-30 domain of inter-alpha-trypsin inhibitor also encodes alpha-1-microglobulin (protein HC). Nucleic Acids Res. 1986 Oct 24;14(20):7839-50. [PubMed:2430261 ]
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