(S)-4-Amino-3-(4-chlorophenyl)butanoic acid

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

What is the (S)-4-Amino-3-(4-chlorophenyl)butanoic acid?

The molecule (S)-4-Amino-3-(4-chlorophenyl)butanoic acid presents a molecular formula of C10H12ClNO2 and its IUPAC name is (3S)-4-amino-3-(4-chlorophenyl)butanoic acid.

S-4-Amino-3-(4-chlorophenyl)butanoic acid is a molecule with the chemical formula C9H10ClNO2. It is a white solid that is soluble in water and organic solvents. It is used as a reagent in organic synthesis..

The molecule has two chiral centers, the amino group and the butanoic acid group. The amino group can exist in two enantiomeric forms, (R)- and (S)-. The butanoic acid group can exist in three enantiomeric forms, (R)-, (S)-, and (RS)-. The molecule can exist in six different stereoisomeric forms..

The (S)-enantiomer is the most abundant in nature and is the form that is used in most biological processes. It is also the form that is used in most synthetic organic reactions..

The (R)-enantiomer is less abundant in nature and is not used in biological processes. It is, however, used in some synthetic organic reactions..

The (RS)-enantiomer is a mixture of the (R)- and (S)-enantiomers in a 1:1 ratio. It is not used in biological processes or in synthetic organic reactions..

The (S)-4-amino-3-(4-chlorophenyl)butanoic acid molecule is used in the synthesis of many different organic molecules. It is also used in the synthesis of pharmaceuticals and agrochemicals..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-4-Amino-3-(4-chlorophenyl)butanoic acid KPYSYYIEGFHWSV-MRVPVSSYSA-N chemical compound 2D structure molecule svg
(S)-4-Amino-3-(4-chlorophenyl)butanoic acid

 

Molecule descriptors

 
IUPAC name(3S)-4-amino-3-(4-chlorophenyl)butanoic acid
InChI codeInChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)/t8-/m1/s1
InChI KeyKPYSYYIEGFHWSV-MRVPVSSYSA-N
SMILESNC[C@@H](CC(=O)O)c1ccc(Cl)cc1

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.

  • (+)-Baclofen
  • (3S)-4-amino-3-(4-chlorophenyl)butanoic acid
  • (L)-Baclofen
  • (S)-4-Amino-3-(4-chloro-phenyl)-butyric acid
  • (S)-4-Amino-3-(4-chlorophenyl)butanoic acid
  • (S)-Baclofen
  • 3OHN4989XM
  • 514A996
  • 66514-99-6
  • A8962
  • AC-22393
  • BACLOFEN, S(+)-
  • BACLOFEN, S-
  • BDBM50032963
  • BENZENEPROPANOIC ACID, .BETA.-(AMINOMETHYL)-4-CHLORO-, (.BETA.S)-
  • Baclofen, (S)-
  • Benzenepropanoic acid, beta-(aminomethyl)-4-chloro-, (betaS)-
  • DB12098
  • L-(+)-Baclofen
  • LS30153
  • Lopac-B-5399
  • NCGC00015156-01
  • NCGC00015156-02
  • NCGC00015156-03
  • NCGC00015156-09
  • NCGC00015156-10
  • NCGC00016565-01
  • NCGC00024579-01
  • Q27257821
  • S(+)-Baclofen
  • Tocris-0417
  • l-Baclofen

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC85733
  • CAS-1134-47-0
  • UNII-3OHN4989XM
  • AKOS025286148
  • CHEMBL302213
  • SCHEMBL19334

Physico-Chemical properties

IUPAC name(3S)-4-amino-3-(4-chlorophenyl)butanoic acid
Molecular formulaC10H12ClNO2
Molecular weight213.661
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity55.32
LogP2.6
Topological polar surface area63.3

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.