(R)-4-Amino-3-hydroxybutanoic acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (R)-4-Amino-3-hydroxybutanoic acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (R)-4-Amino-3-hydroxybutanoic acid?

The molecule (R)-4-Amino-3-hydroxybutanoic acid presents a molecular formula of C4H9NO3 and its IUPAC name is (3R)-4-amino-3-hydroxybutanoic acid.

R-4-Amino-3-hydroxybutanoic acid is an organic molecule with the molecular formula C4H9NO3. It is a white, crystalline solid that is soluble in water. R-4-Amino-3-hydroxybutanoic acid is a chiral molecule, meaning that it has two non-identical forms that are mirror images of each other. The two forms are called enantiomers. R-4-Amino-3-hydroxybutanoic acid is the enantiomer of S-4-amino-3-hydroxybutanoic acid..

R-4-Amino-3-hydroxybutanoic acid is an amino acid that is a component of some proteins. It is also a neurotransmitter in the brain. R-4-Amino-3-hydroxybutanoic acid is an inhibitor of the enzyme monoamine oxidase. Monoamine oxidase is responsible for the breakdown of neurotransmitters in the brain..

R-4-Amino-3-hydroxybutanoic acid has been shown to have antidepressant and anxiolytic effects in animal studies. It has also been shown to improve memory and learning in animal studies..

R-4-Amino-3-hydroxybutanoic acid is being studied as a potential treatment for Alzheimer's disease, depression, and anxiety..

3D structure

Cartesian coordinates

Geometry of (R)-4-Amino-3-hydroxybutanoic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing


(R)-4-Amino-3-hydroxybutanoic acid YQGDEPYYFWUPGO-GSVOUGTGSA-N chemical compound 2D structure molecule svg
(R)-4-Amino-3-hydroxybutanoic acid


Molecule descriptors

IUPAC name(3R)-4-amino-3-hydroxybutanoic acid
InChI codeInChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m1/s1

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-beta-hydroxybutyric acid
  • (3R)-4-Amino-3-hydroxy-butanoic acid
  • (3R)-4-amino-3-hydroxy-butanoic acid;(R)-4-AMINO-3-HYDROXYBUTYRIC ACID
  • (3R)-4-amino-3-hydroxybutanoic acid
  • (3r)-(-)-4-amino-3-hydroxybutanoic acid
  • (R)-(-)-3-Hydroxy-GABA
  • (R)-(-)-4-Amino-3-hydroxybutanoic acid
  • (R)-(-)-Amino-3-hydroxybutanoic acid
  • (R)-(-)-beta-Hydroxy-GABA
  • (R)-4-Amino-3-hydroxybutanoic acid
  • (R)-4-Amino-3-hydroxybutyric acid
  • (R)-GABOB
  • (r)-gamma-amino-beta-hydroxybutyric acid
  • 013A072
  • 592W66MW4A
  • 7013-07-2
  • A836785
  • AC-13944
  • ACT10094
  • BDBM50021187
  • Butanoic acid, 4-amino-3-hydroxy-, (3R)-
  • CS-W005749
  • DB-007982
  • DS-11819
  • MFCD02262047
  • Q27261639
  • R(-)-4-amino-3-hydroxybutanoic acid
  • gamma-Amino-beta-hydroxybutyric acid, (-)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC901811
  • UNII-592W66MW4A
  • AKOS006278832
  • DTXSID60220409
  • CHEMBL290216
  • SCHEMBL2940090

Physico-Chemical properties

IUPAC name(3R)-4-amino-3-hydroxybutanoic acid
Molecular formulaC4H9NO3
Molecular weight119.119
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity26.98
Topological polar surface area83.6

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.