gamma-Aminobutyric acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for gamma-Aminobutyric acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the gamma-Aminobutyric acid?

The molecule gamma-Aminobutyric acid presents a molecular formula of C4H9NO2 and its IUPAC name is 4-aminobutanoic acid.

Gamma-aminobutyric acid (GABA) is a neurotransmitter that plays a critical role in the functioning of the central nervous system. It is the primary inhibitory neurotransmitter in the brain, meaning that it helps to regulate the activity of other neurotransmitters and keeps the brain from becoming over-excited..

GABA belongs throughout the brain and is involved in a wide range of functions, including the regulation of anxiety, mood, and sleep. It is also involved in the regulation of muscle tone and has been shown to have pain-relieving effects..

Deficiencies in GABA have been linked to a number of psychiatric and neurological conditions, including anxiety, depression, epilepsy, and sleep disorders. Supplementation with GABA or medications that increase its availability in the brain have been shown to be effective in the treatment of these conditions..

GABA is synthesized from the amino acid glutamate in a process that requires the enzyme glutamic acid decarboxylase. It is then released from neurons and activates specific receptors in the brain, known as GABA receptors. There are several different types of GABA receptors, and they are found throughout the brain and spinal cord..

In addition to its role as a neurotransmitter, GABA is also involved in the regulation of heart rate, blood pressure, and the secretion of hormones such as insulin and glucagon. It has also been shown to have immune-modulating effects, and may be involved in the development of certain types of cancer..

Summary

From all the above, this molecule is a crucial neurotransmitter that plays a vital role in the functioning of the central nervous system. Its involvement in a wide range of physiological processes makes it an important target for the treatment of various medical conditions..

3D structure

Cartesian coordinates

Geometry of gamma-Aminobutyric acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

gamma-Aminobutyric acid BTCSSZJGUNDROE-UHFFFAOYSA-N chemical compound 2D structure molecule svg
gamma-Aminobutyric acid

 

Molecule descriptors

 
IUPAC name4-aminobutanoic acid
InChI codeInChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI KeyBTCSSZJGUNDROE-UHFFFAOYSA-N
SMILESC(CC(=O)[O-])C[NH3+]

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • .gamma.-Amino-N-butyric acid
  • .gamma.-Amino-butyric acid
  • .gamma.-Aminobutanoic acid
  • .gamma.-Aminobutyric acid
  • .omega.-Aminobutyric acid
  • 20-79-1
  • 2ACZ6IPC6I
  • 3-Carboxypropylamine
  • 4-AMINO-BUTYRATE
  • 4-Amino-butyric acid
  • 4-Aminobutanoic acid
  • 4-Aminobutylate
  • 4-Aminobutyric
  • 4-Aminobutyricacid
  • 4-NH2-but
  • 4-NH3-but
  • 4-amino butyric acid
  • 4-amino-butanoic acid
  • 4-amino-n-[2,3-3H]butyric acid
  • 4-amino-n-butyric acid
  • 4-aminobutanoate
  • 4-aminobutanoic acid (gamma-aminobutyric acid)
  • 4-aminobutyrate
  • 4-aminobutyric acid
  • 4Abu
  • 53504-43-1
  • 56-12-2
  • A 2129
  • A-5290
  • A0282
  • A14934
  • AB00052155_12
  • AI3-26812
  • AM20100372
  • Acide amino-4- butyrique
  • Aminalon
  • Aminalone
  • Aminobutanoic acid
  • Aminobutyric acid, gamma-
  • Aminobutyric acid,-4-
  • BBL008590
  • BCP34675
  • BDBM24183
  • BP-21452
  • BSPBio_002970
  • BUTANOIC ACID,4-AMINO
  • BUTANOIC ACID,4-AMINO 4-AMINO,BUTYRIC ACID
  • Biomol-NT_000230
  • Butanoic acid, 4-amino- (9CI)
  • Butanoic acid, 4-amino-, homopolymer
  • Butyric acid, 4-amino-
  • Butyric acid, 4-amino- (7CI,8CI)
  • C00334
  • C5C3DC27-C105-4D18-8A52-F51978B32D24
  • CCG-38515
  • CCRIS 3721
  • CS-W020704
  • Chemical Name: .gamma.-Aminobutanoic acid
  • D00058
  • D70585
  • DB02530
  • DF 468
  • DSSTox_CID_15106
  • DSSTox_GSID_35106
  • DSSTox_RID_79238
  • DivK1c_000616
  • EPA Pesticide Chemical Code 030802
  • EU-0100005
  • F2191-0196
  • FT-0617569
  • Factor I
  • GABA
  • GAMMA(AMINO)-BUTYRIC ACID
  • GAMMA-AMINO-BUTANOIC ACID
  • GTPL1067
  • GTPL5410
  • Gaballon
  • Gamarex
  • Gamastan
  • Gamma aminobutyrate
  • Gamma-Aminobutyric Acid,(S)
  • Gammagee
  • Gammalon
  • Gammalone
  • Gammar
  • Gammasol
  • Gamulin
  • Globulin, immune human serum
  • HMS1921C06
  • HMS2232P09
  • HMS3260A11
  • HMS501O18
  • HY-N0067
  • IDI1_000616
  • Immu-G
  • Immuglobin
  • KBio1_000616
  • KBio2_000429
  • KBio2_002997
  • KBio2_005565
  • KBio3_002190
  • KBioGR_001297
  • KBioSS_000429
  • KS-5273
  • L000262
  • LMFA01100039
  • LP00005
  • Lopac-A-2129
  • Lopac0_000005
  • MFCD00008226
  • MLS000028505
  • Mielogen
  • Mielomade
  • NCGC00015043-01
  • NCGC00015043-02
  • NCGC00015043-03
  • NCGC00015043-04
  • NCGC00015043-05
  • NCGC00015043-06
  • NCGC00015043-07
  • NCGC00015043-08
  • NCGC00015043-09
  • NCGC00015043-10
  • NCGC00015043-14
  • NCGC00024546-01
  • NCGC00024546-02
  • NCGC00024546-03
  • NCGC00024546-04
  • NCGC00024546-05
  • NCGC00024546-06
  • NCGC00260690-01
  • NH2-(CH2)3-COOH
  • NINDS_000616
  • NSC 27418
  • NSC-27418
  • NSC-32044
  • NSC-45460
  • NSC-51295
  • NSC-757426
  • NSC27418
  • NSC32044
  • NSC45460
  • NSC51295
  • NSC757426
  • Opera_ID_1152
  • Oprea1_584567
  • PDSP1_001275
  • PDSP2_001259
  • Pharmakon1600-01500678
  • Piperidate
  • Piperidic acid
  • Piperidinate
  • Piperidinic acid
  • Q210021
  • Reanal
  • SBI-0049994.P003
  • SDCCGSBI-0049994.P004
  • SGCUT00121
  • SMR000058285
  • SPECTRUM1500678
  • SR-01000075618
  • SR-01000075618-1
  • SR-01000075618-3
  • SR-01000075618-6
  • SR-01000075618-7
  • STK301748
  • STR01523
  • Tocris-0344
  • Vigabatrin EP Impurity D
  • Vigabatrin impurity, .gamma.-aminobutyric acid-
  • WLN: Z3VQ
  • Z955123658
  • [3H]GABA
  • a-Aminobutyric acid
  • aminobutyrate
  • bmse000340
  • bmse000820
  • bmse000871
  • butanoic acid, 4-amino-
  • cid_119
  • g-Aminobutyric acid
  • gam.-Aminobutyric acid
  • gamma Aminobutyric acid
  • gamma-Amino butyric acid
  • gamma-Aminobutanoic acid
  • gamma-Aminobutryic acid
  • gamma-Aminobuttersaeure
  • gamma-Aminobutyric acid
  • gamma-Aminobutyric acid (JAN)
  • gamma-Aminobutyric acid pound>>(c)(3/4)?Aminobutyric acid (GABA)
  • gamma-amino-n-butyric acid
  • gamma-aminobutyrate
  • gamma-aminobutyric acid
  • gamma-aminobutyric-acid
  • omega-Aminobutyrate
  • omega-Aminobutyric acid
  • s4700
  • to_000021
  • w-Aminobutyrate
  • w-Aminobutyric acid
  • y-Aminobutyric acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1532620
  • CAS-56-12-2
  • UNII-2ACZ6IPC6I
  • AKOS000119660
  • BRD-K77245796-001-19-2
  • DTXSID6035106
  • CHEMBL96
  • CHEBI:16865
  • Tox21_110071
  • Tox21_500005
  • EINECS 200-258-6
  • SPBio_000996
  • SCHEMBL4878
  • Spectrum_000049
  • Spectrum2_001208
  • Spectrum3_001385
  • Spectrum4_000809
  • Spectrum5_001425

Physico-Chemical properties

IUPAC name4-aminobutanoic acid
Molecular formulaC4H9NO2
Molecular weight103.12
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity25.1
LogP-3.2
Topological polar surface area67.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.