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Record Information
Version1.0
Creation Date2016-07-13 19:41:09 UTC
Update Date2016-09-23 18:44:33 UTC
LmdbLMDB00045
Secondary Accession NumbersNone
Metabolite Identification
Common NameGamma-Aminobutyric acid
DescriptionGamma-aminobutyric acid (GABA) is an inhibitory neurotransmitter found in the nervous systems of widely divergent species. It is the chief inhibitory neurotransmitter in the vertebrate central nervous system. In vertebrates, GABA acts at inhibitory synapses in the brain. GABA acts by binding to specific transmembrane receptors in the plasma membrane of both pre- and postsynaptic neurons. This binding causes the opening of ion channels to allow either the flow of negatively-charged chloride ions into the cell or positively-charged potassium ions out of the cell. This will typically result in a negative change in the transmembrane potential, usually causing hyperpolarization. Three general classes of GABA receptor are known. These include GABAA and GABAC ionotropic receptors, which are ion channels themselves, and GABAB metabotropic receptors, which are G protein-coupled receptors that open ion channels via intermediaries (G proteins). Neurons that produce GABA as their output are called GABAergic neurons, and have chiefly inhibitory action at receptors in the vertebrate. Medium Spiny Cells are a typical example of inhibitory CNS GABAergic cells. GABA exhibits excitatory actions in insects, mediating muscle activation at synapses between nerves and muscle cells and also the stimulation of certain glands. GABA has also been shown to have excitatory roles in the vertebrate, most notably in the developing cortex. Organisms synthesize GABA from glutamate using the enzyme L-glutamic acid decarboxylase and pyridoxal phosphate as a cofactor. It is worth noting that this involves converting the principal excitatory neurotransmitter (glutamate) into the principal inhibitory one (GABA). Drugs that act as agonists of GABA receptors (known as GABA analogues or GABAergic drugs) or increase the available amount of GABA typically have relaxing, anti-anxiety and anti-convulsive effects. (http://en.wikipedia.org/wiki/GABA) Doses of GABA 1 to 3 g orally also have been used effectively to raise the IQ of mentally retarded persons. GABA is found to be deficient in cerebrospinal fluid and brain in many studies of experimental and animal epilepsy. Benzodiazepines (such as Valium) are useful in status epilepticus because they act on GABA receptors. GABA increases in the brain after administration of many seizure medications. Hence, GABA is clearly an antiepileptic nutrient. Inhibitors of GAM metabolism can also produce convulsions. Spasticity and involuntary movement syndromes, e.g., Parkinson's, Friedreich's ataxia, tardive dyskinesia, and Huntington's chorea are all marked by low GABA when amino acid levels are studied. Trials of 2 to 3 g of GABA given orally have been effective in various epilepsy and spasticity syndromes. Agents that elevate GABA also are useful in lowering hypertension. Three grams orally have been effective in control of blood pressure. GABA is decreased in various encephalopathies. GABA can reduce appetite and is decreased in hypoglycemics. GABA reduces blood sugar in diabetics. Chronic brain syndromes can also be marked by deficiency of GABA; GABA has many promising uses in therapy. Cerebrospinal fluid levels of GABA may be useful in diagnosing very serious diseases. Vitamin B6, manganese, taurine and lysine can increase both GABA synthesis and effects, while aspartic acid and glutamic acid probably inhibit GABA effects. (http://www.dcnutrition.com/AminoAcids/Detail.CFM)The brain's principal inhibitory neurotransmitter, GABA, along with serotonin and norepinephrine, is one of several neurotransmitters that appear to be involved in the pathogenesis of anxiety and mood disorders. There are two principal subtypes of postsynaptic GABA receptor complexes, the GABA-A and GABA-B receptor complexes. Activation of the GABA-B receptor by GABA causes neuronal membrane hyperpolarization and a resultant inhibition of neurotransmitter release. In addition to binding sites for GABA, the GABA-A receptor has binding sites for benzodiazepines, barbiturates, and neurosteroids. GABA-A receptors are coupled to chloride ion channels; activation of the receptor induces increased inward chloride ion flux, resulting in membrane hyperpolarization and neuronal inhibition. After release into the synapse, free GABA that does not bind to either the GABA-A or GABA-B receptor complexes can be taken up by neurons and glial cells. Four different membrane transporter proteins, known as GAT-1, GAT-2, GAT-3, and BGT-1, which differ in their distribution in the CNS, are believed to mediate the uptake of synaptic GABA into neurons and glial cells. The GABA-A receptor subtype regulates neuronal excitability and rapid changes in fear arousal, such as anxiety, panic, and the acute stress response. Drugs that stimulate GABA-A receptors, such as the benzodiazepines and barbiturates, have anxiolytic and anti-seizure effects via GABA-A-mediated reduction of neuronal excitability, which effectively raises the seizure threshold. In support of the anticonvulsant and anxiolytic effects of the GABA-A receptor are findings that GABA-A antagonists produce convulsions in animals and the demonstration that there is decreased GABA-A receptor binding in a positron emission tomography (PET) study of patients with panic disorder. Low plasma GABA has been reported in some depressed patients and, in fact, may be a useful trait marker for mood disorders. (The Role Of GABA In The Pathogenesis And Treatment Of Anxiety And Other Neuropsychiatric Disorders: http://www.vcu-cme.org/gaba/overview.html).
Structure
Thumb
Synonyms
ValueSource
4-Aminobutanoic acidChEBI
4-Aminobutyric acidChEBI
4AbuChEBI
GABAChEBI
GAMMA-AMINO-butanoIC ACIDChEBI
gamma-Amino-N-butyric acidChEBI
gamma-Aminobutanoic acidChEBI
gamma-AminobuttersaeureChEBI
Omega-aminobutyric acidChEBI
Piperidic acidChEBI
Piperidinic acidChEBI
GammalonKegg
4-AminobutyrateKegg
4-AminobutanoateGenerator
g-AMINO-butanoateGenerator
g-AMINO-butanoic acidGenerator
gamma-AMINO-butanoateGenerator
Γ-amino-butanoateGenerator
Γ-amino-butanoic acidGenerator
g-Amino-N-butyrateGenerator
g-Amino-N-butyric acidGenerator
gamma-Amino-N-butyrateGenerator
Γ-amino-N-butyrateGenerator
Γ-amino-N-butyric acidGenerator
g-AminobutanoateGenerator
g-Aminobutanoic acidGenerator
gamma-AminobutanoateGenerator
Γ-aminobutanoateGenerator
Γ-aminobutanoic acidGenerator
g-AminobuttersaeureGenerator
Γ-aminobuttersaeureGenerator
Omega-aminobutyrateGenerator
PiperidateGenerator
PiperidinateGenerator
g-AminobutyrateGenerator
g-Aminobutyric acidGenerator
gamma-AminobutyrateGenerator
Γ-aminobutyrateGenerator
Γ-aminobutyric acidGenerator
3-CarboxypropylamineHMDB
AminalonHMDB
GaballonHMDB
GamarexHMDB
gamma AminobutyrateHMDB
gamma Aminobutyric acidHMDB
GammaloneHMDB
GammarHMDB
GammasolHMDB
MielogenHMDB
MielomadeHMDB
W-AminobutyrateHMDB
W-Aminobutyric acidHMDB
gamma-Aminobutyric acid, calcium salt (2:1)HMDB
gamma-Aminobutyric acid, hydrochlorideHMDB
gamma-Aminobutyric acid, zinc salt (2:1)HMDB
4 Aminobutanoic acidHMDB
4 Aminobutyric acidHMDB
Lithium gabaHMDB
gamma Aminobutyric acid, monolithium saltHMDB
gamma Aminobutyric acid, monosodium saltHMDB
gamma-Aminobutyric acid, monolithium saltHMDB
gamma-Aminobutyric acid, monosodium saltHMDB
Acid, hydrochloride gamma-aminobutyricHMDB
AminaloneHMDB
GABA, lithiumHMDB
Hydrochloride gamma-aminobutyric acidHMDB
gamma Aminobutyric acid, hydrochlorideHMDB
4-Amino-butanoateHMDB
gamma-Aminobutyric acidKEGG
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name4-aminobutanoic acid
Traditional Namegamma(amino)-butyric acid
CAS Registry Number56-12-2
SMILES
NCCCC(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI KeyBTCSSZJGUNDROE-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-2.9ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)4.53ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.46 m³·mol⁻¹ChemAxon
Polarizability10.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-1900000000-f831f79dfcaeffa8b177View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-2de9d92a2cfc7bc655f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-73bbf2ee0803f058dbedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1901000000-85d4bd98af8534428b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-0900000000-6be23968e972a414be51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-9a224763afd8ca892addView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9800000000-d8906d09ca1872a6391cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1900000000-54db7e21790401045519View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1901000000-b047af158215c2b5b8e8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-21ea76dfb0da62031f1dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0901000000-5d60b0a446fd8122f613View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1900000000-f831f79dfcaeffa8b177View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-2de9d92a2cfc7bc655f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-73bbf2ee0803f058dbedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1901000000-85d4bd98af8534428b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0900000000-6be23968e972a414be51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-9a224763afd8ca892addView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-d8906d09ca1872a6391cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-54db7e21790401045519View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1901000000-b047af158215c2b5b8e8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1900000000-1219470a0be188da64e6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-f7117dfaf9d856c95919View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1900000000-e35585a985d8128d044eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-d5f55a414ff1e8c65d9dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9700000000-4b2809309587240dd479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxr-8900000000-ce0d8f44422836cd9965View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-8ce5afb97d7c08821da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9100000000-32c433b2c916697690f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5831aaabdf53f3132ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-9babfd4a6937ecba7318View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-e1c0c1485d846e9b123bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-647d55ecf98850e7a875View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-7c107641a38922c88fcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-86718b349efad6334e3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a1e84e55e4b6c6628d5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0009000000-29c22bf0ed844d09c0afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-1d00adad47e42c60c340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-1900000000-47b195fb74720cc99464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9000000000-a14a52dc59bf9988bb44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-5900000000-20c55b2809389d5ad83bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-eca4c5aefca98751a11eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014j-9000000000-f0783316e09291749409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-81837eb9c0b926cb0e81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0005-9000000000-8b48126992d7fa242636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-7d4636efbc4e5d75872eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4a13b03446b3370ccd43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-dbf4f9e19a35f953a189View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified103 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified66 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified66 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified76 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified87 +/- 14 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified66.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified75.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified86.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified103.1 uMNot AvailableBovine details
SerumDetected and Quantified6.303 uMNot AvailablePorcine details
SerumDetected and Quantified3.782 uMNot AvailablePorcine details
SerumDetected and Quantified4.849 uMNot AvailablePorcine details
SerumDetected and Quantified5.818 uMNot AvailablePorcine details
DrugBank IDDB02530
HMDB IDHMDB0000112
FooDB IDFDB008937
Phenol Explorer IDNot Available
KNApSAcK IDC00001337
BiGG ID34652
BioCyc ID4-AMINO-BUTYRATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGamma-Aminobutyric_acid
Chemspider ID116
ChEBI ID16865
PubChem Compound ID119
Kegg Compound IDC00334
YMDB IDYMDB00335
ECMDB IDECMDB04017
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available