gamma-aminobutyric acid (CHEBI:16865)

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CHEBI:16865 - γ-aminobutyric acid

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ChEBI Name	γ-aminobutyric acid

ChEBI ID	CHEBI:16865

ChEBI ASCII Name	gamma-aminobutyric acid

Definition	A γ-amino acid that is butanoic acid with the amino substituent located at C-4.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40483, CHEBI:1786, CHEBI:20318, CHEBI:193777

Supplier Information	ChemicalBook:CB3184042, eMolecules:476623, ZINC000001532620

Download	Molfile XML SDF

more structures >>

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16 15 0 0 0 0 999 V2000

0.8748 -0.1436 0.8269 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1622 -1.4863 1.2838 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1514 -0.1153 -0.3347 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2902 -1.9555 1.2201 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2676 -2.1893 1.7396 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4695 1.3114 -0.8314 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4354 1.2743 -1.9328 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4908 0.4337 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7933 0.3513 0.4957 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0870 -0.5806 -0.0087 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2350 -0.7024 -1.1736 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4227 -3.0171 1.9941 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4387 1.8004 -1.1892 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8911 1.9097 -0.0206 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6449 2.2430 -2.1808 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2961 0.8665 -1.5611 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 3 1 0 0 0 0

2 4 2 0 0 0 0

2 5 1 0 0 0 0

3 6 1 0 0 0 0

6 7 1 0 0 0 0

1 8 1 0 0 0 0

1 9 1 0 0 0 0

3 10 1 0 0 0 0

3 11 1 0 0 0 0

5 12 1 0 0 0 0

6 13 1 0 0 0 0

6 14 1 0 0 0 0

7 15 1 0 0 0 0

7 16 1 0 0 0 0

M END): 18 ms

reading 16 atoms

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Wikipedia	License
GABA (gamma-aminobutyric acid, γ-aminobutyric acid) is the chief inhibitory neurotransmitter in the developmentally mature mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervous system. GABA is sold as a dietary supplement in many countries. It has been traditionally thought that exogenous GABA (i.e., taken as a supplement) does not cross the blood–brain barrier, but data obtained from more recent research (2010s) in rats describes the notion as being unclear. The carboxylate form of GABA is γ-aminobutyrate.
Read full article at Wikipedia

Formula

C4H9NO2

Net Charge

Average Mass

103.11980

Monoisotopic Mass

103.06333

InChI

InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)

InChIKey

BTCSSZJGUNDROE-UHFFFAOYSA-N

SMILES

NCCCC(O)=O

Metabolite of Species	Details
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). signalling molecule A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell. neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	γ-aminobutyric acid (CHEBI:16865) has functional parent butyric acid (CHEBI:30772) γ-aminobutyric acid (CHEBI:16865) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) γ-aminobutyric acid (CHEBI:16865) has role human metabolite (CHEBI:77746) γ-aminobutyric acid (CHEBI:16865) has role neurotransmitter (CHEBI:25512) γ-aminobutyric acid (CHEBI:16865) has role signalling molecule (CHEBI:62488) γ-aminobutyric acid (CHEBI:16865) is a γ-amino acid (CHEBI:33707) γ-aminobutyric acid (CHEBI:16865) is a monocarboxylic acid (CHEBI:25384) γ-aminobutyric acid (CHEBI:16865) is conjugate acid of γ-aminobutyrate (CHEBI:30566) γ-aminobutyric acid (CHEBI:16865) is tautomer of γ-aminobutyric acid zwitterion (CHEBI:59888)

Incoming	(1S,2S,5S)-2-(4-glutaridylbenzyl)-5-phenylcyclohexan-1-ol (CHEBI:43278) has functional parent γ-aminobutyric acid (CHEBI:16865) 4-(methylamino)butyric acid (CHEBI:37755) has functional parent γ-aminobutyric acid (CHEBI:16865) 4-aminobutanoyl-CoA (CHEBI:15496) has functional parent γ-aminobutyric acid (CHEBI:16865) N-acyl-γ-aminobutyric acid (CHEBI:134018) has functional parent γ-aminobutyric acid (CHEBI:16865) gabapentin (CHEBI:42797) has functional parent γ-aminobutyric acid (CHEBI:16865) gabapentin enacarbil (CHEBI:68840) has functional parent γ-aminobutyric acid (CHEBI:16865) homocarnosine (CHEBI:28050) has functional parent γ-aminobutyric acid (CHEBI:16865) methyl 4-aminobutanoate (CHEBI:42955) has functional parent γ-aminobutyric acid (CHEBI:16865) pregabalin (CHEBI:64356) has functional parent γ-aminobutyric acid (CHEBI:16865) γ-aminobutyrate (CHEBI:30566) is conjugate base of γ-aminobutyric acid (CHEBI:16865) γ-aminobutyric acid zwitterion (CHEBI:59888) is tautomer of γ-aminobutyric acid (CHEBI:16865)

IUPAC Name

4-aminobutanoic acid

Synonyms	Sources
4-aminobutanoic acid	ChEBI
4-Aminobutanoic acid	KEGG COMPOUND
4-aminobutyric acid	ChEBI
4-Aminobutyric acid	KEGG COMPOUND
4Abu	ChEBI
GABA	IUPHAR
GABA	KEGG COMPOUND
GAMMA-AMINO-BUTANOIC ACID	PDBeChem
γ-amino-n-butyric acid	NIST Chemistry WebBook
γ-aminobutanoic acid	NIST Chemistry WebBook
γ-Aminobuttersäure	NIST Chemistry WebBook
γ-aminobutyric acid	NIST Chemistry WebBook
gamma-Aminobutyric acid	KEGG COMPOUND
ω-aminobutyric acid	NIST Chemistry WebBook
piperidic acid	ChemIDplus
piperidinic acid	ChemIDplus

Manual Xrefs	Databases
1262	DrugCentral
2298	BPDB
4-AMINO-BUTYRATE	MetaCyc
ABU	PDBeChem
C00001337	KNApSAcK
C00334	KEGG COMPOUND
D00058	KEGG DRUG
DB02530	DrugBank
Gamma-Aminobutyric_acid	Wikipedia
HMDB0000112	HMDB
LMFA01100039	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
49775	Gmelin Registry Number	Gmelin
56-12-2	CAS Registry Number	ChemIDplus
56-12-2	CAS Registry Number	NIST Chemistry WebBook
906818	Reaxys Registry Number	Reaxys

Citations

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Li H, Qiu T, Chen Y, Cao Y (2011)
Separation of gamma-aminobutyric acid from fermented broth.
Journal of industrial microbiology & biotechnology 38, 1955-1959 [PubMed:21614609]
[show Abstract]

Doepner RF, Geigerseder C, Frungieri MB, Gonzalez-Calvar SI, Calandra RS, Raemsch R, Fohr K, Kunz L, Mayerhofer A (2005)
Insights into GABA receptor signalling in TM3 Leydig cells.
Neuroendocrinology 81, 381-390 [PubMed:16276116]
[show Abstract]

Zhao Z, Baldo BA, O'Brien RM, Plomley RF (2000)
Reaction with, and fine structural recognition of polyamines by human IgE antibodies.
Molecular immunology 37, 233-240 [PubMed:10930630]
[show Abstract]

Minta J, Fung M (1999)
Transcriptional modulation of the human complement factor I gene in Hep G2 cells by protein kinase C activation.
Molecular and cellular biochemistry 201, 111-123 [PubMed:10630630]
[show Abstract]
This study examined the role of the protein kinase C (PKC) signalling pathway in the regulation of expression of human complement factor I (CFI) gene. The production of CFI by Hep G2 cells was enhanced in a dose- and time-dependent fashion by 12-O-tetradecanoyl-1,2-phorbol 13-acetate (TPA), a potent PKC activator. 4Alpha-phorbol didecanoate, an inactive phorbol ester, had no effect on CFI synthesis. The TPA-dependent increase in CFI secretion was correlated with an increase in CFI mRNA levels. Forskolin, a cAMP-inducing agent, augmented the TPA response. W7, an inhibitor of protein kinase A and genistein, an inhibitor of protein tyrosine kinase(s) both did not prevent the increase in CFI expression mediated by TPA. However, calphostin C, a specific inhibitor of PKC, abolished the TPA-induced increase in CFI mRNA levels. Down regulation of intracellular PKC levels by prior exposure of Hep G2 cells to a high concentration of TPA also blocked the increase in CFI mRNA levels induced by TPA suggesting that the TPA effects were mediated via activation of PKC. mRNA decay studies indicated that the half-life of CFI mRNA in TPA-induced cells was not significantly different from control. Nuclear run-on transcriptional assays on the other hand demonstrated that whereas the CFI gene is transcribed under basal conditions in Hep G2 cells, TPA induced a 3-4 fold increase in the transcription rate of CFI gene in 24 h. The transcription rate of GAPDH gene did not change, indicating that the effects were not general on gene transcription. Transient transfections of Hep G2 cells with chloramphenicol acetyltransferase reporter gene (CAT) constructs containing a series of sequential 5' deletions of the CFI promoter and CAT assays showed that the sequence between -136 and -130, containing an AP-1 consensus sequence (TGAGTCA) was required for the TPA response. This observation was substantiated by the finding that mutation of this AP-1 site to TttaTCA or TtAtcCA abolished the TPA responsiveness. The enhancement of the activity of transfected chimeric CAT constructs by TPA was abrogated by calphostin C and by pyrrolidine dithiocarbamate (an inhibitor of NF-kappaB and AP-1 transactivation). These results indicate that TPA regulation of CFI gene requires PKC signalling and is mediated by via a TPA response element (TRE) in the CFI promoter region located at -136/-130 and involves the transactivation of AP-1 and NF-kappaB transcription factors. We suggest that PKC may be one of the intracellular pathways that control CFI gene expression and that cellular processes (involving growth factors, hormones, cytokines etc.) that activate PKC may upregulate the expression of the CFI gene.

Last Modified

15 January 2019

General Comment
2011-01-15	The chief inhibitory neurotransmitter in the mammalian central nervous system.

CHEBI:16865 - γ-aminobutyric acid

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