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): 16 ms

reading 16 atoms

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Wikipedia	License
[object Object]
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

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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