Record Information
Version1.0
Creation date2015-05-07 19:21:37 UTC
Update date2018-05-29 01:54:52 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
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
OntologyShould have ontology for this compound
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
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
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
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