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Identification
YMDB IDYMDB00335
Namegamma-Aminobutyric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiongamma-Aminobutyrate (GABA) is a four-carbon non-protein amino acid conserved from bacteria to plants and vertebrates. GABA was originally discovered in plants in 1949, but interest shifted to animals when it was found that GABA occurs at high levels in the brain, as a neurotransmitter. In plants and in animals, GABA is mainly metabolized via a short pathway composed of three enzymes, called the GABA shunt because it bypasses two steps of the TCA cycle. In S. cerevisiae GABA plays an important role in nitrogen utilization and oxidative stress tolerance. GABA accumulates either through permease-mediated uptake, or by intracellular production via L-glutamate degradation in the glutamate degradation IX (via 4-aminobutyrate) pathway. [Biocyc 4-AMINO-BUTYRATE and PWY-6536 and PWY3O-210]
Structure
Thumb
Synonyms
  • .gamma.-Aminobutyric acid
  • 3-Carboxypropylamine
  • 4-(Glutamylamino)butanoate
  • 4-Amino-butyrat
  • 4-Amino-n-butyric acid
  • 4-Aminobutanoate
  • 4-Aminobutanoic acid
  • 4-aminobutanoic acid ion (1-)
  • 4-Aminobutylate
  • 4-Aminobutyrate
  • 4-Aminobutyric acid
  • Aminalon
  • Aminobutyric acid,-4-, alpha
  • Butanoic acid, 4-amino-
  • Butyric acid, 4-amino-
  • GABA
  • Gaballon
  • Gamarex
  • Gamastan
  • Gamma aminobutyrate
  • Gamma aminobutyric acid
  • gamma-aminobutanoate
  • Gamma-aminobutyrate
  • gamma-aminobutyrate anion
  • Gamma-aminobutyric acid
  • gamma-Glutamyl-GABA
  • gamma-Glutamyl-gamma-aminobutyrate
  • gamma.-Amino-butyric acid
  • Gammagee
  • Gammalon
  • Gammalone
  • Gammar
  • Gammasol
  • Mielogen
  • Mielomade
  • omega-Aminobutyrate
  • omega-Aminobutyric acid
  • Piperidate
  • Piperidic acid
  • Piperidinate
  • Piperidinic acid
  • Reanal
  • w-Aminobutyrate
  • w-Aminobutyric acid
  • 4Abu
  • GAMMA-AMINO-butanoIC ACID
  • gamma-Amino-N-butyric acid
  • gamma-Aminobutanoic acid
  • gamma-Aminobuttersaeure
  • g-AMINO-butanoate
  • g-AMINO-butanoic acid
  • gamma-AMINO-butanoate
  • Γ-amino-butanoate
  • Γ-amino-butanoic acid
  • g-Amino-N-butyrate
  • g-Amino-N-butyric acid
  • gamma-Amino-N-butyrate
  • Γ-amino-N-butyrate
  • Γ-amino-N-butyric acid
  • g-Aminobutanoate
  • g-Aminobutanoic acid
  • Γ-aminobutanoate
  • Γ-aminobutanoic acid
  • g-Aminobuttersaeure
  • Γ-aminobuttersaeure
  • g-Aminobutyrate
  • g-Aminobutyric acid
  • Γ-aminobutyrate
  • Γ-aminobutyric acid
  • gamma-Aminobutyric acid, calcium salt (2:1)
  • gamma-Aminobutyric acid, hydrochloride
  • gamma-Aminobutyric acid, zinc salt (2:1)
  • 4 Aminobutanoic acid
  • 4 Aminobutyric acid
  • Lithium gaba
  • gamma Aminobutyric acid, monolithium salt
  • gamma Aminobutyric acid, monosodium salt
  • gamma-Aminobutyric acid, monolithium salt
  • gamma-Aminobutyric acid, monosodium salt
  • Acid, hydrochloride gamma-aminobutyric
  • Aminalone
  • GABA, lithium
  • Hydrochloride gamma-aminobutyric acid
  • gamma Aminobutyric acid, hydrochloride
  • 4-Amino-butanoate
CAS number56-12-2
WeightAverage: 103.1198
Monoisotopic: 103.063328537
InChI KeyBTCSSZJGUNDROE-UHFFFAOYSA-N
InChIInChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
IUPAC Name4-aminobutanoic acid
Traditional IUPAC Namegamma(amino)-butyric acid
Chemical FormulaC4H9NO2
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])N([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting point203 °C
Experimental Properties
PropertyValueReference
Water Solubility1300 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.17 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • Cell Envelope
  • Cytoplasm
  • Endoplasmic Reticulum
  • Extracellular
  • Lipid Particle
  • Mitochondrion
Organoleptic Properties
Flavour/OdourSource
MeatyFDB008937
SavoryFDB008937
SMPDB Pathways
4-aminobutanoate degradationPW002382 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Arginine and proline metabolismec00330 Map00330
Butanoate metabolismec00650 Map00650
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
gamma-Aminobutyric acid + Oxoglutaric acidL-Glutamic acid + Succinic acid semialdehyde
KEGG Reactions
water + 4-Acetamidobutanoic acidAcetic acid + gamma-Aminobutyric acid
Oxoglutaric acid + gamma-Aminobutyric acidL-Glutamic acid + Succinic acid semialdehyde
NAD + 4-aminobutanal + waterNADH + gamma-Aminobutyric acid + hydron
L-Glutamic acid + hydronCarbon dioxide + gamma-Aminobutyric acid
Glycine + alpha-D-ribose 5-phosphate + hydron + L-Cysteine + O-Acetyl-L-homoserinePyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Coleman, S. T., Fang, T. K., Rovinsky, S. A., Turano, F. J., Moye-Rowley, W. S. (2001). "Expression of a glutamate decarboxylase homologue is required for normal oxidative stress tolerance in Saccharomyces cerevisiae." J Biol Chem 276:244-250.11031268
Synthesis Reference:Minoshima, Ryoichi. Preparation of gamma-aminobutyric acid with unripened beans. PCT Int. Appl. (2007), 25pp.
External Links:
ResourceLink
CHEBI ID16865
HMDB IDHMDB00112
Pubchem Compound ID119
Kegg IDC00334
ChemSpider ID116
FOODB IDFDB008937
WikipediaGamma-Aminobutyric_acid
BioCyc ID4-AMINO-BUTYRATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(+) + H(2)O = an acid + NADH
Gene Name:
ALD4
Uniprot ID:
P46367
Molecular weight:
56723.19922
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Minor mitochondrial aldehyde dehydrogenase isoform. Plays a role in regulation or biosynthesis of electron transport chain components. Involved in the biosynthesis of acetate during anaerobic growth on glucose
Gene Name:
ALD5
Uniprot ID:
P40047
Molecular weight:
56620.39844
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
An aldehyde + NADP(+) + H(2)O → an acid + NADPH.
General function:
Involved in transaminase activity
Specific function:
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N- acetyl-L-glutamate 5-semialdehyde + L-glutamate
Gene Name:
ARG8
Uniprot ID:
P18544
Molecular weight:
46681.10156
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate → N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Required for the degradation of gamma-aminobutyric acid (GABA), which is important for utilization of GABA as nitrogen source and for oxidative stress tolerance. Deaminates GABA to succinate semialdehyde, which in turn is converted to succinate by the succinate-semialdehyde dehydrogenase UGA2. Cannot transaminate beta-alanine (BAL)
Gene Name:
UGA1
Uniprot ID:
P17649
Molecular weight:
52945.69922
Reactions
4-aminobutanoate + 2-oxoglutarate → succinate semialdehyde + L-glutamate.
General function:
Involved in glutamate decarboxylase activity
Specific function:
L-glutamate = 4-aminobutanoate + CO(2)
Gene Name:
GAD1
Uniprot ID:
Q04792
Molecular weight:
65989.5
Reactions
L-glutamate → 4-aminobutanoate + CO(2).

Transporters

General function:
Involved in transport
Specific function:
Required for high-affinity proline transport. May be responsible for proline recognition and probably also for proline translocation across the plasma membrane. Also function as non- specific GABA permease. Can also transport alanine and glycine
Gene Name:
PUT4
Uniprot ID:
P15380
Molecular weight:
68786.79688
General function:
Involved in transport
Specific function:
Required for high-affinity, high-specificity GABA transport. Also transports putrescine
Gene Name:
UGA4
Uniprot ID:
P32837
Molecular weight:
61872.30078