| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 10:00:40 UTC |
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| Updated at | 2025-02-11 15:45:12 UTC |
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| NP-MRD ID | NP0153363 |
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| Natural Product DOI | https://doi.org/10.57994/2413 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | kainic acid |
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| Description | Kainic acid, also known as kainate or acide kainique, belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups. Glutamate is produced by the cell's metabolic processes and there are four major classifications of glutamate receptors: NMDA receptors, AMPA receptors, kainate receptors, and the metabotropic glutamate receptors. Kainic acid is a very strong basic compound (based on its pKa). Such damage and death of neurons is referred to as an excitotoxic lesion. It is important to note that both chemical and electrical lesions potentially cause additional damage to the brain due to the very nature of the inserted electrode or cannula. In addition to inducing seizures, kainic acid is excitotoxic and epileptogenic. Called "Kainin-sou" or "Makuri" in Japan. kainic acid is found in Apis cerana, Chondria armata and Digenea simplex. Kainate receptors likely control a sodium channel that produces excitatory postsynaptic potentials (EPSPs) when glutamate binds. |
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| Structure | [H][C@@]1(CN[C@]([H])(C(O)=O)[C@@]1([H])CC(O)=O)C(C)=C InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1 |
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| Synonyms | | Value | Source |
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| (2S-(2alpha,3beta,4beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid | ChEBI | | Acide kainique | ChEBI | | Acido kainico | ChEBI | | Acidum kainicum | ChEBI | | alpha- Kainic acid | ChEBI | | alpha-Kainic acid | ChEBI | | Digenic acid | ChEBI | | Digenin | ChEBI | | Digensaeure | ChEBI | | Helminal | ChEBI | | Kainsaeure | ChEBI | | L-alpha-Kainic acid | ChEBI | | Kainate | Kegg | | (2S-(2a,3b,4b))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetate | Generator | | (2S-(2a,3b,4b))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid | Generator | | (2S-(2alpha,3beta,4beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetate | Generator | | (2S-(2Α,3β,4β))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetate | Generator | | (2S-(2Α,3β,4β))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid | Generator | | a- Kainate | Generator | | a- Kainic acid | Generator | | alpha- Kainate | Generator | | Α- kainate | Generator | | Α- kainic acid | Generator | | a-Kainate | Generator | | a-Kainic acid | Generator | | alpha-Kainate | Generator | | Α-kainate | Generator | | Α-kainic acid | Generator | | Digenate | Generator | | L-a-Kainate | Generator | | L-a-Kainic acid | Generator | | L-alpha-Kainate | Generator | | L-Α-kainate | Generator | | L-Α-kainic acid | Generator | | Acid, digenic | MeSH | | Acid, kainic | MeSH |
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| Chemical Formula | C10H15NO4 |
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| Average Mass | 213.2304 Da |
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| Monoisotopic Mass | 213.10011 Da |
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| IUPAC Name | (2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid |
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| Traditional Name | kainic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]1(CN[C@]([H])(C(O)=O)[C@@]1([H])CC(O)=O)C(C)=C |
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| InChI Identifier | InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1 |
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| InChI Key | VLSMHEGGTFMBBZ-OOZYFLPDSA-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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| HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | HOMO2DJ NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | 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, 499.83, C2D6OS, simulated) | [email protected] | Not Available | Not Available | 2024-05-09 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups. |
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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 | Kainoids |
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| Alternative Parents | |
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| Substituents | - Kainoid skeleton
- Proline or derivatives
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Dicarboxylic acid or derivatives
- Pyrrolidine
- Amino acid
- Carboxylic acid
- Secondary aliphatic amine
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Carbonyl group
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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