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 ZINC000013508431
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Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss. Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness. Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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Formula C4H9NO2
Net Charge 0
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.
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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 Types Sources
10630630 PubMed citation Europe PMC
10930630 PubMed citation Europe PMC
16276116 PubMed citation Europe PMC
21614609 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
Last Modified
15 January 2019
General Comment
2011-01-15 The chief inhibitory neurotransmitter in the mammalian central nervous system.