Canmetcon
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Identification
YMDB IDYMDB00886
NameL-Cystine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCystine is an oxidized dimeric form of the amino acid cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions is partially responsible for the formation of the gluten matrix in bread.
Structure
Thumb
Synonyms
  • (-)-Cystine
  • (R-(R*,R*))-3,3'-Dithiobis
  • [R-(R*,R*)]-3,3'-Dithiobis
  • 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate
  • 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid
  • 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate
  • 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid
  • 3,3'-Dithiobis
  • 3,3'-dithiobis-L-Alanine
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoate
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid
  • 3,3'-Dithiodialanine
  • b,b'-Diamino-b,b'-dicarboxydiethyl disulfide
  • b,b'-Dithiodialanine
  • beta,beta'-Dithiobisalanine
  • beta,beta'-Dithiodialanine
  • Bis(b-amino-b-carboxyethyl) disulfide
  • Bis(b-amino-beta-carboxyethyl) disulfide
  • Cysteine disulfide
  • Cystin
  • Cystine
  • Cystine acid
  • D(+)-3,3'-Dithiobis(2-aminopropanoate
  • D(+)-3,3'-Dithiobis(2-aminopropanoic acid
  • Dicysteine
  • Gelucystine
  • L-(-)-Cystine
  • L-Cysteine disulfide
  • L-Cystin
  • l-Cystine
  • Oxidized L-cysteine
  • (R,R)-3,3'-Dithiobis(2-aminopropanoic acid)
  • (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)
  • beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide
  • Bis(beta-amino-beta-carboxyethyl) disulfide
  • e921
  • L-alpha-Diamino-beta-dithiolactic acid
  • L-Dicysteine
  • (R,R)-3,3'-Dithiobis(2-aminopropanoate)
  • (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)
  • b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide
  • b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide
  • beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide
  • Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide
  • Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide
  • b,Beta'-dithiodialanine
  • Β,beta'-dithiodialanine
  • Bis(b-amino-b-carboxyethyl) disulphide
  • Bis(beta-amino-beta-carboxyethyl) disulphide
  • Bis(β-amino-β-carboxyethyl) disulfide
  • Bis(β-amino-β-carboxyethyl) disulphide
  • L-a-Diamino-b-dithiolactate
  • L-a-Diamino-b-dithiolactic acid
  • L-alpha-Diamino-beta-dithiolactate
  • L-Α-diamino-β-dithiolactate
  • L-Α-diamino-β-dithiolactic acid
  • L Cystine
  • Copper cystinate
CAS number56-89-3
WeightAverage: 240.3
Monoisotopic: 240.023848262
InChI KeyLEVWYRKDKASIDU-IMJSIDKUSA-N
InChIInChI=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
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional IUPAC NameL-cystine
Chemical FormulaC6H12N2O4S2
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])SSC([H])([H])[C@]([H])(N([H])[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Organic disulfide
  • Dialkyldisulfide
  • Amino acid
  • Sulfenyl compound
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point260.5 °C
Experimental Properties
PropertyValueReference
Water Solubility0.19 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-5.08 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP-3.2ALOGPS
logP-5.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity54.87 m³·mol⁻¹ChemAxon
Polarizability22.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • vacuole
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16283
HMDB IDHMDB00192
Pubchem Compound ID67678
Kegg IDC00491
ChemSpider ID60997
FOODB IDFDB012672
WikipediaCystine
BioCyc IDCYSTINE

Transporters

General function:
Involved in L-cystine transmembrane transporter activity
Specific function:
Transport cystine out of vacuoles/endodomes
Gene Name:
ERS1
Uniprot ID:
P17261
Molecular weight:
30116.0