Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2022-01-23 16:35:53 UTC |
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NP-MRD ID | NP0001028 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | L-Glutamic acid |
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Description | Glutamic acid (Glu), also known as L-glutamic acid or as glutamate, the name of its anion, 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-glutamic acid is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Glutamic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans it is a non-essential amino acid and can be synthesized via alanine or aspartic acid via alpha-ketoglutarate and the action of various transaminases. Glutamate also plays an important role in the body's disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase leading to alpha-ketoglutarate. In many respects glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: Damage to mitochondria from excessively high intracellular Ca2+. Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization (http://En.Wikipedia.Org/wiki/Glutamic_acid). Glutamate was discovered in 1866 when it was extracted from wheat gluten (from where it got its name. Glutamate has an important role as a food additive and food flavoring agent. In 1908, Japanese researcher Kikunae Ikeda identified brown crystals left behind after the evaporation of a large amount of kombu broth (a Japanese soup) as glutamic acid. These crystals, when tasted, reproduced a salty, savory flavor detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate. |
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Structure | InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 |
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Synonyms | Value | Source |
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(S)-2-Aminopentanedioic acid | ChEBI | (S)-Glutamic acid | ChEBI | Acide glutamique | ChEBI | Acido glutamico | ChEBI | Acidum glutamicum | ChEBI | E | ChEBI | Glu | ChEBI | Glutamate | ChEBI | GLUTAMIC ACID | ChEBI | L-Glu | ChEBI | L-Glutaminic acid | ChEBI | L-Glutaminsaeure | ChEBI | (S)-2-Aminopentanedioate | Generator | (S)-Glutamate | Generator | L-Glutaminate | Generator | L-Glutamate | Generator | (2S)-2-Aminopentanedioate | HMDB | (2S)-2-Aminopentanedioic acid | HMDB | (S)-(+)-Glutamate | HMDB | (S)-(+)-Glutamic acid | HMDB | 1-Amino-propane-1,3-dicarboxylate | HMDB | 1-Amino-propane-1,3-dicarboxylic acid | HMDB | 1-Aminopropane-1,3-dicarboxylate | HMDB | 1-Aminopropane-1,3-dicarboxylic acid | HMDB | 2-Aminoglutarate | HMDB | 2-Aminoglutaric acid | HMDB | 2-Aminopentanedioate | HMDB | 2-Aminopentanedioic acid | HMDB | a-Aminoglutarate | HMDB | a-Aminoglutaric acid | HMDB | a-Glutamate | HMDB | a-Glutamic acid | HMDB | Aciglut | HMDB | alpha-Aminoglutarate | HMDB | alpha-Aminoglutaric acid | HMDB | alpha-Glutamate | HMDB | alpha-Glutamic acid | HMDB | Aminoglutarate | HMDB | Aminoglutaric acid | HMDB | Glt | HMDB | Glusate | HMDB | Glut | HMDB | Glutacid | HMDB | Glutamicol | HMDB | Glutamidex | HMDB | Glutaminate | HMDB | Glutaminic acid | HMDB | Glutaminol | HMDB | Glutaton | HMDB | L-(+)-Glutamate | HMDB | L-(+)-Glutamic acid | HMDB | L-a-Aminoglutarate | HMDB | L-a-Aminoglutaric acid | HMDB | L-alpha-Aminoglutarate | HMDB | L-alpha-Aminoglutaric acid | HMDB | D Glutamate | HMDB | Glutamate, potassium | HMDB | Glutamic acid, (D)-isomer | HMDB | L Glutamic acid | HMDB | D-Glutamate | HMDB | L Glutamate | HMDB | Aluminum L glutamate | HMDB | Aluminum L-glutamate | HMDB | L-Glutamate, aluminum | HMDB | Potassium glutamate | HMDB | 2-Acetamido-2-deoxy-D-glucose | HMDB | D-GlcNAc | HMDB | N-Acetyl-D-glucosamine | HMDB | N-Acetylchitosamine | HMDB | N Acetyl D glucosamine | HMDB | 2 Acetamido 2 deoxy D glucose | HMDB | 2 Acetamido 2 deoxyglucose | HMDB | 2-Acetamido-2-deoxyglucose | HMDB | Acetylglucosamine | HMDB | 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine | HMDB | N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine | HMDB | N-Choloylglycine | HMDB | 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine | HMDB | 3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine | HMDB | N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine | HMDB | N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine | HMDB | Glycocholate | HMDB | Glycine cholate | HMDB | Glycocholic acid, sodium salt | HMDB | Cholylglycine | HMDB | Glycocholate sodium | HMDB | 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine | HMDB | 3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide | HMDB | 3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine | HMDB | 3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide | HMDB | Glycoreductodehydrocholic acid | HMDB | Glycylcholate | HMDB | Glycylcholic acid | HMDB | N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide | HMDB | N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide | HMDB | N-Choloyl-glycine | HMDB | 3-Hydroxy-1,3,5(10)-estratrien-17-one | HMDB | Follicular hormone | HMDB | Folliculin | HMDB | Oestrone | HMDB | (+)-Estrone | HMDB | 1,3,5(10)-Estratrien-3-ol-17-one | HMDB | 3-Hydroxy-17-keto-estra-1,3,5-triene | HMDB | 3-Hydroxyestra-1,3,5(10)-trien-17-one | HMDB | 3-Hydroxyestra-1,3,5(10)-triene-17-one | HMDB | 3-Hydroxyoestra-1,3,5(10)-trien-17-one | HMDB | D1,3,5(10)-Estratrien-3-ol-17-one | HMDB | Estrone, (+-)-isomer | HMDB | Hyrex brand OF estrone | HMDB | Estrone, (9 beta)-isomer | HMDB | Estrovarin | HMDB | Kestrone | HMDB | Wehgen | HMDB | Estrone, (8 alpha)-isomer | HMDB | Hauck brand OF estrone | HMDB | Unigen | HMDB | Vortech brand OF estrone | HMDB | alpha,beta-Hydroxypropionic acid | HMDB | D-GroA | HMDB | R-Glyceric acid | HMDB | Glycerate | HMDB | (R)-Glycerate | HMDB | a,b-Hydroxypropionate | HMDB | a,b-Hydroxypropionic acid | HMDB | alpha,beta-Hydroxypropionate | HMDB | Α,β-hydroxypropionate | HMDB | Α,β-hydroxypropionic acid | HMDB | R-Glycerate | HMDB | (R)-Glyceric acid | HMDB | D-Glycerate | HMDB | D-Glyceric acid | HMDB | (2R)-2,3-Dihydroxypropanoic acid | HMDB | (R)-2,3-Dihydroxypropanoic acid | HMDB | D-2,3-Dihydroxypropanoic acid | HMDB | 1-Amino-2-hydroxyethane | HMDB | 2-Amino-1-ethanol | HMDB | 2-Amino-ethanol | HMDB | 2-Aminoethan-1-ol | HMDB | 2-Aminoethyl alcohol | HMDB | 2-Hydroxyethylamine | HMDB | Aethanolamin | HMDB | Aminoethanol | HMDB | beta-Aminoethanol | HMDB | beta-Aminoethyl alcohol | HMDB | beta-Ethanolamine | HMDB | beta-Hydroxyethylamine | HMDB | Colamine | HMDB | ETA | HMDB | Glycinol | HMDB | Hea | HMDB | MEA | HMDB | MONOETHANOLAMINE | HMDB | b-Aminoethanol | HMDB | Β-aminoethanol | HMDB | b-Aminoethyl alcohol | HMDB | Β-aminoethyl alcohol | HMDB | b-Ethanolamine | HMDB | Β-ethanolamine | HMDB | b-Hydroxyethylamine | HMDB | Β-hydroxyethylamine | HMDB | 2-Aminoethanol | HMDB | 2-Ethanolamine | HMDB | 2-Hydroxyethanamine | HMDB | Envision conditioner PDD 9020 | HMDB | Ethylolamine | HMDB | H-Glycinol | HMDB | Monoaethanolamin | HMDB | Olamine | HMDB | 2 Aminoethanol | HMDB | (3R,4S,5R)-5-[(1R)-1-Carboxy-2,2-difluoro-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate | HMDB | (1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate | HMDB | (1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid | HMDB | (1S)-2-[(3-O-beta-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid | HMDB | (1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate | HMDB | (1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid | HMDB |
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Chemical Formula | C5H9NO4 |
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Average Mass | 147.1293 Da |
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Monoisotopic Mass | 147.05316 Da |
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IUPAC Name | (2S)-2-aminopentanedioic acid |
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Traditional Name | L-glutamic acid |
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CAS Registry Number | 56-86-0 |
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SMILES | N[C@@H](CCC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 |
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InChI Key | WHUUTDBJXJRKMK-VKHMYHEASA-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 | | | 2022-01-23 | 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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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-08-05 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-08-05 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-07-26 | View Spectrum |
| 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 glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 | Glutamic acid and derivatives |
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Alternative Parents | |
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Substituents | - Glutamic acid or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Organic oxide
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- 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 | |
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Predicted Properties | |
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General References | - Molinari F, Raas-Rothschild A, Rio M, Fiermonte G, Encha-Razavi F, Palmieri L, Palmieri F, Ben-Neriah Z, Kadhom N, Vekemans M, Attie-Bitach T, Munnich A, Rustin P, Colleaux L: Impaired mitochondrial glutamate transport in autosomal recessive neonatal myoclonic epilepsy. Am J Hum Genet. 2005 Feb;76(2):334-9. Epub 2004 Dec 8. [PubMed:15592994 ]
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