Identification
YMDB IDYMDB00847
NameD-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
  • (2S,2'S)-3,3'-dithiobis(2-aminopropanoic acid)
  • cystine D-form
  • (2S,2's)-3,3'-Dithiobis(2-aminopropanoate)
  • Copper cystinate
  • L Cystine
  • L-Cystine
  • Cystine
CAS number349-46-2
WeightAverage: 240.3
Monoisotopic: 240.023848262
InChI KeyLEVWYRKDKASIDU-QWWZWVQMSA-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-/m1/s1
IUPAC Name(2S)-2-amino-3-{[(2S)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional IUPAC NameD-cystine
Chemical FormulaC6H12N2O4S2
SMILESN[C@H](CSSC[C@@H](N)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • D-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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility0.1 mg/mL at 25 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
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
Polarizability22.43 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 PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-9400000000-211575093fd775db5d54JSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • Zenk, M. H., Schmitt, J. H. (1965). "[Purification and properties of acetyl-CoA: D-amino acid-alpha-N-acetyltransferase from yeast]." Biochem Z 342:54-65.5847960
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID35494
HMDB IDNot Available
Pubchem Compound ID6857538
Kegg IDNot Available
ChemSpider ID5256874
FOODB IDNot Available
WikipediaCystine
BioCyc IDNot Available

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:
HPA3
Uniprot ID:
P39979
Molecular weight:
20698.5
Reactions
acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid