L-cystine

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

What is the L-cystine?

The molecule L-cystine presents a molecular formula of C6H12N2O4S2 and its IUPAC name is (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid.

L-cystine is an amino acid that is produced naturally in the body. It is also found in some foods, such as eggs, meat, and dairy products. L-cystine is important for the formation of proteins and enzymes in the body. It is also involved in the metabolism of iron and copper. L-cystine supplements are sometimes used to treat certain medical conditions, such as cystinuria and sickle cell anemia..

3D structure

Cartesian coordinates

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

2D drawing

 

L-cystine LEVWYRKDKASIDU-IMJSIDKUSA-N chemical compound 2D structure molecule svg
L-cystine

 

Molecule descriptors

 
IUPAC name(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
InChI codeInChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChI KeyLEVWYRKDKASIDU-IMJSIDKUSA-N
SMILESN[C@@H](CSSC[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.

  • (-)-Cystine
  • (2R)-2-amino-3-[[(2R)-2-amino-2-carboxy-ethyl]disulfanyl]propanoic acid
  • (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
  • (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
  • (2R)-2-azanyl-3-[[(2R)-2-azanyl-3-oxidanyl-3-oxidanylidene-propyl]disulfanyl]propanoic acid
  • (2R,2'R)-3,3'-disulfanediylbis(2-aminopropanoic acid)
  • (H-Cys-OH)2
  • (H-Cys-OH)2 (Disulfide bond)
  • (R,R)-3,3'-Dithiobis(2-aminopropionic Acid)
  • (R,R)-3,3'-Dithiobis(2-aminopropionicacid)
  • (R,R)-3,3'-dithiobis(2-aminopropanoic acid)
  • (R-(R*,R*))-3,3'-Dithiobis
  • (R-(R*,R*))-3,3'-Dithiobis(2-aminopropanoic acid)
  • 064C228
  • 1-Cystine
  • 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate
  • 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid
  • 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate
  • 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid
  • 2079930-29-1
  • 3,3'-Dithiobis
  • 3,3'-Dithiobis(2-aminopropanoic acid)
  • 3,3'-Dithiobis(2-aminopropanoic acid), (R-(R*,R*))-
  • 3,3'-Dithiobis-L-alanine
  • 3,3'-Dithiodialanine
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoate
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid
  • 3,3-DISULFANEDIYLBIS((2R)-2-AMINOPROPANOIC ACID)
  • 48TCX9A1VT
  • 56-89-3
  • AC-11189
  • ACETYLCYSTEINE IMPURITY A (L-CYSTINE)
  • AI3-09064
  • AM81644
  • AS-12654
  • Alanine, 3,3'-dithiobis-
  • Alanine, 3,3'-dithiodi-
  • BRN 1728094
  • Bis(b-amino-b-carboxyethyl) disulfide
  • Bis(b-amino-beta-carboxyethyl) disulfide
  • Bis(beta-amino-beta-carboxyethyl) disulfide
  • Bis(beta-amino-beta-carboxyethyl)disulfide
  • C00491
  • CCG-36355
  • CCRIS 5822
  • CS-0008930
  • Cysteine disulfide
  • Cystin
  • Cystine (L)-
  • Cystine (L-Cystine)
  • Cystine (USAN/INN)
  • Cystine acid
  • Cystine, L-
  • Cystine, L- (8CI)
  • Cystine, NIST(R) SRM(R) 143d
  • Cystine,d
  • D(+)-3,3'-Dithiobis(2-aminopropanoate
  • D(+)-3,3'-Dithiobis(2-aminopropanoic acid
  • D03636
  • DB00138
  • DD82F461-3F8F-4624-9E2C-0272A9FA79ED
  • DSSTox_CID_26418
  • DSSTox_GSID_46418
  • DSSTox_RID_81596
  • Dicysteine
  • EC 200-296-3
  • GTPL5413
  • Gelucystine
  • HY-N0394
  • IYY
  • L-(-)-Cystine
  • L-Alanine, 3,3'-dithiobis-
  • L-Cysteine disulfide
  • L-Cystin
  • L-Cystine (9CI)
  • L-Cystine (JP17)
  • L-Cystine, non-animal source
  • L-Dicysteine
  • L-alpha-Diamino-beta-dithiolactic acid
  • L-cystine
  • M06021
  • MFCD00064228
  • NCGC00164531-01
  • NCGC00166006-01
  • NCGC00166006-02
  • NSC 13203
  • NSC-13203
  • Oxidized L-cysteine
  • Propanoic acid, 3,3'-dithiobis(2-amino-, (R-(R*,R*))-
  • Q408626
  • S-(((R)-2-amino-2-carboxyethyl)thio)cysteine
  • S-CYSTEINYL CYSTEINE
  • Z2786051647
  • [R-(R*,R*)]-3,3'-Dithiobis
  • b,b'-Diamino-b,b'-dicarboxydiethyl disulfide
  • b,b'-Dithiodialanine
  • beta,beta'-Diamino-beta,beta'-dicarboxydiethyl disulfide
  • beta,beta'-Diamino-beta,beta'-dicarboxydiethyldisulfide
  • beta,beta'-Dithioalanine, L-
  • beta,beta'-Dithiobisalanine
  • beta,beta'-Dithiodialanine
  • bmse000035
  • cystine
  • s4808

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1532673
  • CAS-56-89-3
  • UNII-48TCX9A1VT
  • AKOS015898645
  • DTXSID2046418
  • CHEMBL590540
  • CHEBI:16283
  • Tox21_112162
  • Tox21_112162_1
  • EINECS 200-296-3
  • SCHEMBL10226

Physico-Chemical properties

IUPAC name(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
Molecular formulaC6H12N2O4S2
Molecular weight240.3
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity55.10
LogP0.6
Topological polar surface area177.2

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.