Survey with prize
Record Information
Version1.0
Creation date2015-05-07 19:21:37 UTC
Update date2019-11-26 03:21:45 UTC
Primary IDFDB030489
Secondary Accession Numbers
  • FDB008937
Chemical Information
FooDB Name4-aminobutanoate
DescriptionGamma-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).
CAS Number56-12-2
Structure
Thumb
Synonyms
SynonymSource
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
4-AminobutyrateKegg
GammalonKegg
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
Predicted Properties
PropertyValueSource
Water Solubility365 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H9NO2
IUPAC name4-aminobutanoic acid
InChI IdentifierInChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI KeyBTCSSZJGUNDROE-UHFFFAOYSA-N
Isomeric SMILESNCCCC(O)=O
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-dbf4f9e19a35f953a189Spectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00dj-1900000000-f831f79dfcaeffa8b177Spectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-2de9d92a2cfc7bc655f4Spectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-73bbf2ee0803f058dbedSpectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-1901000000-85d4bd98af8534428b5aSpectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-0900000000-6be23968e972a414be51Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-9a224763afd8ca892addSpectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-9800000000-d8906d09ca1872a6391cSpectrum
GC-MS4-Aminobutyric acid, 2 TMS, GC-MS Spectrumsplash10-0udi-1900000000-54db7e21790401045519Spectrum
GC-MS4-Aminobutyric acid, 3 TMS, GC-MS Spectrumsplash10-00di-1901000000-b047af158215c2b5b8e8Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-21ea76dfb0da62031f1dSpectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-0901000000-5d60b0a446fd8122f613Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00dj-1900000000-f831f79dfcaeffa8b177Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-2de9d92a2cfc7bc655f4Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-73bbf2ee0803f058dbedSpectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1901000000-85d4bd98af8534428b5aSpectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-0900000000-6be23968e972a414be51Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-9a224763afd8ca892addSpectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-9800000000-d8906d09ca1872a6391cSpectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-54db7e21790401045519Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00di-1901000000-b047af158215c2b5b8e8Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-00dj-1900000000-1219470a0be188da64e6Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-f7117dfaf9d856c95919Spectrum
GC-MS4-Aminobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-e35585a985d8128d044eSpectrum
Predicted GC-MS4-Aminobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-d5f55a414ff1e8c65d9dSpectrum
Predicted GC-MS4-Aminobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-9700000000-4b2809309587240dd479Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxr-8900000000-ce0d8f44422836cd9965Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-8ce5afb97d7c08821da3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9100000000-32c433b2c916697690f8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5831aaabdf53f3132ae5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-9babfd4a6937ecba7318Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-e1c0c1485d846e9b123bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-647d55ecf98850e7a875Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-7c107641a38922c88fcaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-86718b349efad6334e3aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a1e84e55e4b6c6628d5dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0009000000-29c22bf0ed844d09c0afSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-1d00adad47e42c60c340Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-1900000000-47b195fb74720cc99464Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9000000000-a14a52dc59bf9988bb44Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-5900000000-20c55b2809389d5ad83bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-eca4c5aefca98751a11eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014j-9000000000-f0783316e09291749409Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-81837eb9c0b926cb0e81Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0005-9000000000-8b48126992d7fa242636Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-7d4636efbc4e5d75872eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4a13b03446b3370ccd43Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference