L-Cystine (ECMDB00192) (M2MDB000081)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (480)
Record Information
Version2.0
Creation Date2012-05-31 10:23:28 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00192
Identification
Name:L-Cystine
DescriptionCystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. The L-cysteine transporter, YdeD, is required for the tolerance of E. coli cells to hydrogen peroxide. L-cystine, a product from the oxidation of L-cysteine by hydrogen peroxide, is imported back into the cytoplasm in a manner dependent on the periplasmic L-cystine-binding protein (FliY). This protein is involved in the recycling of the oxidized L-cysteine and is important for the hydrogen peroxide resistance of E. coli. In E. coli the L-cysteine/L-cystine shuttle system plays an important role in oxidative stress tolerance through providing a reducing equivalent to the periplasm in E. coli.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (-)-Cystine
  • (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-carboxy-ethyl)disulphanyl-propanoate
  • 2-Amino-3-(2-amino-2-carboxy-ethyl)disulphanyl-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'-diamino-b,b'-dicarboxydiethyl disulphide
  • B,b'-Dithiodialanine
  • b,Beta'-diamino-b,b'-dicarboxydiethyl disulfide
  • b,Beta'-diamino-b,b'-dicarboxydiethyl disulphide
  • b,Beta'-dithiobisalanine
  • b,Beta'-dithiodialanine
  • Beta,beta'-Diamino-b,b'-dicarboxydiethyl disulfide
  • Beta,beta'-Diamino-b,b'-dicarboxydiethyl disulphide
  • Beta,beta'-Dithiobisalanine
  • Beta,beta'-Dithiodialanine
  • Bis(b-amino-b-carboxyethyl) disulfide
  • Bis(b-amino-b-carboxyethyl) disulphide
  • Bis(b-amino-beta-carboxyethyl) disulfide
  • Bis(b-amino-beta-carboxyethyl) disulphide
  • Bis(b-amino-β-carboxyethyl) disulfide
  • Bis(b-amino-β-carboxyethyl) disulphide
  • Cysteine disulfide
  • Cysteine disulphide
  • Cystin
  • Cystine
  • Cystine acid
  • D(+)-3,3'-Dithiobis(2-aminopropanoate
  • D(+)-3,3'-Dithiobis(2-aminopropanoate)
  • D(+)-3,3'-Dithiobis(2-aminopropanoic acid
  • D(+)-3,3'-Dithiobis(2-aminopropanoic acid)
  • Dicysteine
  • Gelucystine
  • L-(-)-Cystine
  • L-Cysteine disulfide
  • L-Cysteine disulphide
  • L-Cystin
  • L-Cystine
  • Oxidized L-cysteine
  • [R-(R*,R*)]-3,3'-Dithiobis
  • β,Beta'-diamino-b,b'-dicarboxydiethyl disulfide
  • β,Beta'-diamino-b,b'-dicarboxydiethyl disulphide
  • β,Beta'-dithiobisalanine
  • β,Beta'-dithiodialanine
Chemical Formula:C6H12N2O4S2
Weight:Average: 240.3
Monoisotopic: 240.023848262
InChI Key:LEVWYRKDKASIDU-IMJSIDKUSA-N
InChI:InChI=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
CAS number:56-89-3
IUPAC Name:(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional IUPAC Name:L-cystine
SMILES:N[C@@H](CSSC[C@H](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
State:Solid
Charge:0
Melting point:260.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.19 mg/mL [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:Cytoplasm
Reactions:
L-Cystine + Water <> Pyruvic acid + Ammonia + Thiocysteine
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0950000000-a803bc05843192dd737dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0940000000-f82b905ef9e7c9e47552View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-49b9a52a8387d6d6f272View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014j-1970000000-9576699202733d4fd7edView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0950000000-a803bc05843192dd737dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9850000000-49b9a52a8387d6d6f272View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-1970000000-9576699202733d4fd7edView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0930000000-7cb336c3f272fd0fcd6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0920000000-1c414573da4bbe4a66ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-9400000000-211575093fd775db5d54View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0076-9112000000-ee49e3b674a4f8bb9ecdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0890000000-51a32ee40240e45646bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9700000000-4054924ddfb90f120e67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9100000000-085d45702e61de0f8e4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9710000000-9321541af2ad89bd0478View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0090000000-041bfa55cb183f42f454View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0190000000-3611e8b6715129842130View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0190000000-dbafdd64edad14af9281View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0290000000-6b80d283287249ba4b87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-000i-0390000000-c091ce388dfcbd339e3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0079-0690000000-c808ac294a0bc182c5ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0079-0970000000-36297b29c4ef45c658e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00dr-0940000000-a8c735a0f9082cfd7c7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1920000000-9d55705325536cca5eb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1910000000-cd18de2585913152e907View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-00di-1900000000-3118609f8682bee472c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-00di-2900000000-213ccc3c067486ff9444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00di-3900000000-df68db23afd937a9a75dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-00di-4900000000-b46d26f57a194d2ff648View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-00di-6900000000-5535cccb24de733cada3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006w-2970000000-b80e0aef184b74ce7a36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00re-4910000000-a09277c5a6bfc432eb79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xu-9600000000-0518bfcaab380952c123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3590000000-aa667d3c092c5af3ae7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-5910000000-122bd251359ca80b184cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9300000000-bbb14e684ff7c06e7916View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000x-9000000000-ae0f516d71e6a49fe52fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
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  • Allen JW, Shanker G, Tan KH, Aschner M: The consequences of methylmercury exposure on interactive functions between astrocytes and neurons. Neurotoxicology. 2002 Dec;23(6):755-9. Pubmed: 12520765
  • Behr T, Becker W, Hannappel E, Goldenberg DM, Wolf F: Targeting of liver metastases of colorectal cancer with IgG, F(ab')2, and Fab' anti-carcinoembryonic antigen antibodies labeled with 99mTc: the role of metabolism and kinetics. Cancer Res. 1995 Dec 1;55(23 Suppl):5777s-5785s. Pubmed: 7493346
  • Coe FL, Evan A, Worcester E: Kidney stone disease. J Clin Invest. 2005 Oct;115(10):2598-608. Pubmed: 16200192
  • Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kubilus J, MacDonald MJ, Baden HP: Epidermal proteins of cultured human and bovine keratinocytes. Biochim Biophys Acta. 1979 Jun 19;578(2):484-92. Pubmed: 486533
  • Mitchell BF, Chibbar R: Synthesis and metabolism of oxytocin in late gestation in human decidua. Adv Exp Med Biol. 1995;395:365-80. Pubmed: 8713992
  • Mogil'naia GM, Shubich MG: [Comparison of the histochemical bases of epidermis differentiation in vertebrates] Arkh Anat Gistol Embriol. 1976 Mar;70(3):46-52. Pubmed: 1275714
  • Orakzai N, Hanbury DC, Farrington K: Screening for biochemical abnormalities in urolithiasis patients. J Ayub Med Coll Abbottabad. 2004 Apr-Jun;16(2):60-3. Pubmed: 15455621
  • Park M, Helip-Wooley A, Thoene J: Lysosomal cystine storage augments apoptosis in cultured human fibroblasts and renal tubular epithelial cells. J Am Soc Nephrol. 2002 Dec;13(12):2878-87. Pubmed: 12444206
  • Peters T, Thaete C, Wolf S, Popp A, Sedlmeier R, Grosse J, Nehls MC, Russ A, Schlueter V: A mouse model for cystinuria type I. Hum Mol Genet. 2003 Sep 1;12(17):2109-20. Pubmed: 12923163
  • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
  • Rossi S, Herrine SK, Navarro VJ: Cystinosis as a cause of noncirrhotic portal hypertension. Dig Dis Sci. 2005 Jul;50(7):1372-5. Pubmed: 16047489
  • Rumpold H, Mascher K, Untergasser G, Plas E, Hermann M, Berger P: Trans-differentiation of prostatic stromal cells leads to decreased glycoprotein hormone alpha production. J Clin Endocrinol Metab. 2002 Nov;87(11):5297-303. Pubmed: 12414905
  • Sakhaee K: Pathogenesis and medical management of cystinuria. Semin Nephrol. 1996 Sep;16(5):435-47. Pubmed: 8890399
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Sonies BC, Almajid P, Kleta R, Bernardini I, Gahl WA: Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Medicine (Baltimore). 2005 May;84(3):137-46. Pubmed: 15879904
  • Terada T, Maeda H, Okamoto K, Nishinaka T, Mizoguchi T, Nishihara T: Modulation of glutathione S-transferase activity by a thiol/disulfide exchange reaction and involvement of thioltransferase. Arch Biochem Biophys. 1993 Jan;300(1):495-500. Pubmed: 8424686
  • Tezuka T, Takahashi M: The cystine-rich envelope protein from human epidermal stratum corneum cells. J Invest Dermatol. 1987 Jan;88(1):47-51. Pubmed: 3794387
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Worcester EM, Coe FL, Evan AP, Parks JH: Reduced renal function and benefits of treatment in cystinuria vs other forms of nephrolithiasis. BJU Int. 2006 Jun;97(6):1285-90. Pubmed: 16686727
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16283
HMDB IDHMDB00192
Pubchem Compound ID67678
Kegg IDC00491
ChemSpider ID60997
WikipediaCystine
BioCyc IDCYSTINE
EcoCyc IDCYSTINE

Enzymes

Protein Details
1. Cystathionine beta-lyase metC
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
Gene Name:
metC
Uniprot ID:
P06721
Molecular weight:
43212
Reactions
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.
Protein Details
2. Protein malY
General function:
Involved in transferase activity
Specific function:
Acts as a beta-cystathionase and as a repressor of the maltose regulon
Gene Name:
malY
Uniprot ID:
P23256
Molecular weight:
43641
Reactions
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.