Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 19:21:37 UTC |
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Update date | 2019-11-26 03:21:45 UTC |
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Primary ID | FDB030489 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | 4-aminobutanoate |
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Description | Gamma-aminobutyric acid, also known as gaba or 4-aminobutanoic acid, belongs to gamma amino acids and derivatives class of compounds. Those are amino acids having a (-NH2) group attached to the gamma carbon atom. Thus, gamma-aminobutyric acid is considered to be a fatty acid lipid molecule. Gamma-aminobutyric acid is soluble (in water) and a weakly acidic compound (based on its pKa). Gamma-aminobutyric acid can be synthesized from butyric acid. Gamma-aminobutyric acid is also a parent compound for other transformation products, including but not limited to, (1S,2S,5S)-2-(4-glutaridylbenzyl)-5-phenylcyclohexan-1-ol, 4-(methylamino)butyric acid, and pregabalin. Gamma-aminobutyric acid can be found in a number of food items such as watercress, sour cherry, peach, and cardoon, which makes gamma-aminobutyric acid a potential biomarker for the consumption of these food products. Gamma-aminobutyric acid can be found primarily in most biofluids, including urine, cerebrospinal fluid (CSF), blood, and feces, as well as throughout most human tissues. Gamma-aminobutyric acid exists in all living species, ranging from bacteria to humans. In humans, gamma-aminobutyric acid is involved in a couple of metabolic pathways, which include glutamate metabolism and homocarnosinosis. Gamma-aminobutyric acid is also involved in few metabolic disorders, which include 2-hydroxyglutric aciduria (D and L form), 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, hyperinsulinism-hyperammonemia syndrome, and succinic semialdehyde dehydrogenase deficiency. Moreover, gamma-aminobutyric acid is found to be associated with alzheimer's disease, hyper beta-alaninemia, tuberculous meningitis, and hepatic encephalopathy. Gamma-aminobutyric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. gamma-Aminobutyric acid (γ-Aminobutyric acid) (GABA ) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervous system. In humans, GABA is also directly responsible for the regulation of muscle tone . Chronically high levels of GABA are associated with at least 5 inborn errors of metabolism including: D-2-Hydroxyglutaric Aciduria, 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency, GABA-Transaminase Deficiency, Homocarnosinosis and Succinic semialdehyde dehydrogenase deficiency (T3DB). |
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CAS Number | 56-12-2 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Aminobutanoic acid | ChEBI | 4-Aminobutyric acid | ChEBI | 4Abu | ChEBI | GABA | ChEBI | GAMMA-AMINO-butanoIC ACID | ChEBI | gamma-Amino-N-butyric acid | ChEBI | gamma-Aminobutanoic acid | ChEBI | gamma-Aminobuttersaeure | ChEBI | Omega-aminobutyric acid | ChEBI | Piperidic acid | ChEBI | Piperidinic acid | ChEBI | 4-Aminobutyrate | Kegg | Gammalon | Kegg | 4-Aminobutanoate | Generator | g-AMINO-butanoate | Generator | g-AMINO-butanoic acid | Generator | gamma-AMINO-butanoate | Generator | Γ-amino-butanoate | Generator | Γ-amino-butanoic acid | Generator | g-Amino-N-butyrate | Generator | g-Amino-N-butyric acid | Generator | gamma-Amino-N-butyrate | Generator | Γ-amino-N-butyrate | Generator | Γ-amino-N-butyric acid | Generator | g-Aminobutanoate | Generator | g-Aminobutanoic acid | Generator | gamma-Aminobutanoate | Generator | Γ-aminobutanoate | Generator | Γ-aminobutanoic acid | Generator | g-Aminobuttersaeure | Generator | Γ-aminobuttersaeure | Generator | Omega-aminobutyrate | Generator | Piperidate | Generator | Piperidinate | Generator | g-Aminobutyrate | Generator | g-Aminobutyric acid | Generator | gamma-Aminobutyrate | Generator | Γ-aminobutyrate | Generator | Γ-aminobutyric acid | Generator | 3-Carboxypropylamine | HMDB | Aminalon | HMDB | Gaballon | HMDB | Gamarex | HMDB | gamma Aminobutyrate | HMDB | gamma Aminobutyric acid | HMDB | Gammalone | HMDB | Gammar | HMDB | Gammasol | HMDB | Mielogen | HMDB | Mielomade | HMDB | W-Aminobutyrate | HMDB | W-Aminobutyric acid | HMDB | gamma-Aminobutyric acid, calcium salt (2:1) | HMDB | gamma-Aminobutyric acid, hydrochloride | HMDB | gamma-Aminobutyric acid, zinc salt (2:1) | HMDB | 4 Aminobutanoic acid | HMDB | 4 Aminobutyric acid | HMDB | Lithium gaba | HMDB | gamma Aminobutyric acid, monolithium salt | HMDB | gamma Aminobutyric acid, monosodium salt | HMDB | gamma-Aminobutyric acid, monolithium salt | HMDB | gamma-Aminobutyric acid, monosodium salt | HMDB | Acid, hydrochloride gamma-aminobutyric | HMDB | Aminalone | HMDB | GABA, lithium | HMDB | Hydrochloride gamma-aminobutyric acid | HMDB | gamma Aminobutyric acid, hydrochloride | HMDB | 4-Amino-butanoate | HMDB | gamma-Aminobutyric acid | KEGG |
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Predicted Properties | |
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Chemical Formula | C4H9NO2 |
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IUPAC name | 4-aminobutanoic acid |
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InChI Identifier | InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7) |
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InChI Key | BTCSSZJGUNDROE-UHFFFAOYSA-N |
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Isomeric SMILES | NCCCC(O)=O |
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Average Molecular Weight | 103.1198 |
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Monoisotopic Molecular Weight | 103.063328537 |
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Classification |
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Description | Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon 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 | Gamma amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Gamma amino acid or derivatives
- Amino fatty acid
- Straight chain fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Amine
- Hydrocarbon derivative
- 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Biological role: Industrial application: |
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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 | Not Available | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-dbf4f9e19a35f953a189 | 2014-09-20 | View Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00dj-1900000000-f831f79dfcaeffa8b177 | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-1900000000-2de9d92a2cfc7bc655f4 | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-1900000000-73bbf2ee0803f058dbed | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-1901000000-85d4bd98af8534428b5a | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-0900000000-6be23968e972a414be51 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-9a224763afd8ca892add | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-9800000000-d8906d09ca1872a6391c | Spectrum | GC-MS | 4-Aminobutyric acid, 2 TMS, GC-MS Spectrum | splash10-0udi-1900000000-54db7e21790401045519 | Spectrum | GC-MS | 4-Aminobutyric acid, 3 TMS, GC-MS Spectrum | splash10-00di-1901000000-b047af158215c2b5b8e8 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-21ea76dfb0da62031f1d | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-0901000000-5d60b0a446fd8122f613 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00dj-1900000000-f831f79dfcaeffa8b177 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-2de9d92a2cfc7bc655f4 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-73bbf2ee0803f058dbed | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1901000000-85d4bd98af8534428b5a | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-0900000000-6be23968e972a414be51 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-9a224763afd8ca892add | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-9800000000-d8906d09ca1872a6391c | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-0udi-1900000000-54db7e21790401045519 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00di-1901000000-b047af158215c2b5b8e8 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-00dj-1900000000-1219470a0be188da64e6 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-0udi-0900000000-f7117dfaf9d856c95919 | Spectrum | GC-MS | 4-Aminobutyric acid, non-derivatized, GC-MS Spectrum | splash10-0006-1900000000-e35585a985d8128d044e | Spectrum | Predicted GC-MS | 4-Aminobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-9000000000-d5f55a414ff1e8c65d9d | Spectrum | Predicted GC-MS | 4-Aminobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fk9-9700000000-4b2809309587240dd479 | 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) | splash10-0uxr-8900000000-ce0d8f44422836cd9965 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0005-9000000000-8ce5afb97d7c08821da3 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0005-9100000000-32c433b2c916697690f8 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-5831aaabdf53f3132ae5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-9000000000-9babfd4a6937ecba7318 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-9000000000-e1c0c1485d846e9b123b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-647d55ecf98850e7a875 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-7c107641a38922c88fca | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-86718b349efad6334e3a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-a1e84e55e4b6c6628d5d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-0009000000-29c22bf0ed844d09c0af | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0udi-0900000000-1d00adad47e42c60c340 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0udi-1900000000-47b195fb74720cc99464 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-001i-9000000000-a14a52dc59bf9988bb44 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0udi-5900000000-20c55b2809389d5ad83b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-9000000000-eca4c5aefca98751a11e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-014j-9000000000-f0783316e09291749409 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0005-9000000000-81837eb9c0b926cb0e81 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0005-9000000000-8b48126992d7fa242636 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000i-9000000000-7d4636efbc4e5d75872e | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9100000000-655f9d93a35bfa537583 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00ku-9000000000-4a334d5e272576f62403 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-4a13b03446b3370ccd43 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9100000000-655f9d93a35bfa537583 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00ku-9000000000-4a334d5e272576f62403 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | 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 | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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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 | 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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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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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 | Not Available |
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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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