L-cystathionine

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

What is the L-cystathionine?

The molecule L-cystathionine presents a molecular formula of C7H14N2O4S and its IUPAC name is (2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid.

L-cystathionine is a molecule that is produced in the body during the metabolism of the amino acid cysteine. It is a byproduct of the breakdown of the amino acid methionine. L-cystathionine participes in the synthesis of the amino acids taurine and glutathione. It is also a precursor of the important antioxidant glutathione..

L-cystathionine is produced in the liver and kidney. It is also found in the brain, where it participes in the synthesis of the neurotransmitter GABA. L-cystathionine is present in a variety of foods, including meat, fish, and poultry. It is also found in some plant foods, such as broccoli and Brussels sprouts..

L-cystathionine has a number of important health benefits. It has been shown to protect the liver from damage caused by alcohol and other toxins. L-cystathionine also helps to detoxify the body by binding to heavy metals, such as lead and mercury..

L-cystathionine supplements are available in health food stores and online. The recommended dose is 500 mg per day..

3D structure

Cartesian coordinates

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

2D drawing

 

L-cystathionine ILRYLPWNYFXEMH-WHFBIAKZSA-N chemical compound 2D structure molecule svg
L-cystathionine

 

Molecule descriptors

 
IUPAC name(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
InChI codeInChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
InChI KeyILRYLPWNYFXEMH-WHFBIAKZSA-N
SMILESN[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O

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.

  • (2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
  • (2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid
  • (2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
  • (R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine
  • (S)-2-amino-4-((R)-2-amino-2-carboxyethylthio)butanoic acid
  • 375YFJ481O
  • 56-88-2
  • AS-56691
  • Butanoic acid, 2-amino-4-((2-amino-2-carboxyethyl)thio)-, (R-(R*,S*))-
  • Butanoic acid, 2-amino-4-[(2-amino-2-carboxyethyl)thio]-, [R-(R*,S*)]-
  • C02291
  • CS-W010465
  • Cystathionine (6CI,7CI)
  • Cystathionine, L-
  • Cystathionine, L- (8CI)
  • DB-008956
  • E79085
  • FD1436D6-F116-4693-B9DB-B8A83420BD09
  • GTPL5173
  • HY-W009749
  • L-(+)-Cystathionine
  • L-Homocysteine, S-((2R)-2-amino-2-carboxyethyl)-
  • L-Homocysteine, S-(2-amino-2-carboxyethyl)-, (R)-
  • L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]-
  • L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]- (9CI)
  • L-cystathionine
  • MFCD00036685
  • Q28529685
  • S-(2-amino-2-carboxyethyl)homocysteine
  • S-(beta-amino-beta-carboxyethyl)homocysteine
  • S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteine
  • [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoate
  • [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoic acid
  • cystathionine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1532680
  • UNII-375YFJ481O
  • AKOS030240717
  • DTXSID20971384
  • CHEBI:17482
  • EINECS 200-295-8
  • SCHEMBL81862

Physico-Chemical properties

IUPAC name(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
Molecular formulaC7H14N2O4S
Molecular weight222.262
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity52.31
LogP0.3
Topological polar surface area151.9

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.