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Cystine (YMDB00861)

Identification
YMDB IDYMDB00861
NameCystine
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
MOLSDFPDBSMILESInChI
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-carboxyethyl)dithio]propanoate
  • 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid
  • 3, 3'-Dithiobis(2-aminopropanoic acid)
  • 3,3'-Dithiobis
  • 3,3'-dithiobis-L-Alanine
  • 3,3'-Dithiobis(2-aminopropanoic acid)
  • 3,3'-Dithiobis(2-aminopropionic acid)
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoate
  • 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid
  • 3,3'-Dithiodialanine
  • Alanine, 3, 3'-dithiobis-
  • Alanine, 3,3'-dithiobis-
  • Alanine, 3,3'-dithiodi-
  • alpha-Diamino-beta-dithiolactic acid
  • b,b'-Diamino-b,b'-dicarboxydiethyl disulfide
  • b,b'-Dithiodialanine
  • beta,beta'-Diamino-beta,beta'-dicarboxydiethyl disulfide
  • beta,beta'-Dithiobisalanine
  • beta,beta'-Dithiodialanine
  • Bis(b-amino-b-carboxyethyl) disulfide
  • Bis(b-amino-beta-carboxyethyl) disulfide
  • Bis(beta-amino-beta-carboxyethyl) disulfide
  • cistina
  • Cysteine disulfide
  • Cystin
  • Cystine
  • Cystine acid
  • Cystine, L-
  • D(+)-3,3'-Dithiobis(2-aminopropanoate
  • D(+)-3,3'-Dithiobis(2-aminopropanoic acid
  • Dicysteine
  • Gelucystine
  • Gelucystine (L form)
  • L-(-)-Cystine
  • L-3,3'-dithiodialanine
  • l-alpha-diamino-beta-dithiolactic acid
  • L-Cysteine disulfide
  • L-Cystin
  • L-Cystine
  • l-dicysteine
  • Nephrin
  • Oxidized L-cysteine
  • Propanoic acid, 3, {3'-dithiobis[2-amino-,} {[R-(R*,R*)]-}
  • Propanoic acid, 3,3'-dithiobis(2-amino-, (R-(R*,R*))-
  • Zystin
  • (R,R)-3,3'-Dithiobis(2-aminopropanoic acid)
  • (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)
  • e921
  • (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
  • 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid
  • L Cystine
  • Copper cystinate
CAS number56-89-3
WeightAverage: 240.3
Monoisotopic: 240.023848262
InChI KeyLEVWYRKDKASIDU-UHFFFAOYSA-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)
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional IUPAC NameL-cystine
Chemical FormulaC6H12N2O4S2
SMILESNC(CSSCC(N)C(O)=O)C(O)=O
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 LocationsNot Available
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0950000000-a803bc05843192dd737dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0940000000-f82b905ef9e7c9e47552JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-49b9a52a8387d6d6f272JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014j-1970000000-9576699202733d4fd7edJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0950000000-a803bc05843192dd737dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9850000000-49b9a52a8387d6d6f272JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-1970000000-9576699202733d4fd7edJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0930000000-7cb336c3f272fd0fcd6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0920000000-1c414573da4bbe4a66ddJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-9400000000-211575093fd775db5d54JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0076-9112000000-ee49e3b674a4f8bb9ecdJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0890000000-51a32ee40240e45646bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9700000000-4054924ddfb90f120e67JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9100000000-085d45702e61de0f8e4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9710000000-9321541af2ad89bd0478JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0090000000-041bfa55cb183f42f454JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0190000000-3611e8b6715129842130JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0190000000-dbafdd64edad14af9281JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0290000000-6b80d283287249ba4b87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-000i-0390000000-c091ce388dfcbd339e3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0079-0690000000-c808ac294a0bc182c5ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0079-0970000000-36297b29c4ef45c658e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00dr-0940000000-a8c735a0f9082cfd7c7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1920000000-9d55705325536cca5eb2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1910000000-cd18de2585913152e907JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-00di-1900000000-3118609f8682bee472c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-00di-2900000000-213ccc3c067486ff9444JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00di-3900000000-df68db23afd937a9a75dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-00di-4900000000-b46d26f57a194d2ff648JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-00di-6900000000-5535cccb24de733cada3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006w-2970000000-b80e0aef184b74ce7a36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00re-4910000000-a09277c5a6bfc432eb79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xu-9600000000-0518bfcaab380952c123JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3590000000-aa667d3c092c5af3ae7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-5910000000-122bd251359ca80b184cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9300000000-bbb14e684ff7c06e7916JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000x-9000000000-ae0f516d71e6a49fe52fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • ROMANO, A. H., NICKERSON, W. J. (1954). "Cystine reductase of pea seeds and yeasts." J Biol Chem 208:409-416.13174550
  • Nagai, S., Black, S. (1968). "A thiol-disulfide transhydrogenase from yeast." J Biol Chem 243:1942-1947.5646485
Synthesis Reference:Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry (2002), 67(24), 8625-8630.
External Links:
ResourceLink
CHEBI ID17376
HMDB IDHMDB00192
Pubchem Compound ID67678
Kegg IDC00491
ChemSpider ID575
FOODB IDFDB012672
WikipediaCystine
BioCyc IDCYSTINE