Showing metabocard for L-Cystine (BMDB0000192)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:26:32 UTC
Update Date2020-06-04 21:10:52 UTC
MCDB ID BMDB0000192
Secondary Accession Numbers
  • BMDB00192
Metabolite Identification
Common NameL-Cystine
DescriptionCystine, also known as L-dicysteine or E921, 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. Cystine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Cystine exists in all living species, ranging from bacteria to humans. Cystine has been found to be associated with several diseases known as molybdenum cofactor deficiency, schizophrenia, parkinson's disease, and colorectal cancer; also cystine has been linked to the inborn metabolic disorders including fumarase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)ChEBI
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)ChEBI
3,3'-Dithiobis-L-alanineChEBI
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfideChEBI
beta,Beta'-dithiodialanineChEBI
Bis(beta-amino-beta-carboxyethyl) disulfideChEBI
e921ChEBI
L-alpha-Diamino-beta-dithiolactic acidChEBI
L-DicysteineChEBI
Oxidized L-cysteineChEBI
(R,R)-3,3'-Dithiobis(2-aminopropanoate)Generator
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)Generator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfideGenerator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphideGenerator
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphideGenerator
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfideGenerator
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphideGenerator
b,Beta'-dithiodialanineGenerator
Β,beta'-dithiodialanineGenerator
Bis(b-amino-b-carboxyethyl) disulfideGenerator
Bis(b-amino-b-carboxyethyl) disulphideGenerator
Bis(beta-amino-beta-carboxyethyl) disulphideGenerator
Bis(β-amino-β-carboxyethyl) disulfideGenerator
Bis(β-amino-β-carboxyethyl) disulphideGenerator
L-a-Diamino-b-dithiolactateGenerator
L-a-Diamino-b-dithiolactic acidGenerator
L-alpha-Diamino-beta-dithiolactateGenerator
L-Α-diamino-β-dithiolactateGenerator
L-Α-diamino-β-dithiolactic acidGenerator
(-)-CystineHMDB
(R-(R*,r*))-3,3'-dithiobisHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoateHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acidHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoateHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acidHMDB
3,3'-DithiobisHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoateHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acidHMDB
3,3'-DithiodialanineHMDB
b,B'-diamino-b,b'-dicarboxydiethyl disulfideHMDB
b,B'-dithiodialanineHMDB
beta,Beta'-dithiobisalanineHMDB
Bis(b-amino-beta-carboxyethyl) disulfideHMDB
Cysteine disulfideHMDB
CystinHMDB
CystineHMDB
Cystine acidHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoateHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoic acidHMDB
DicysteineHMDB
GelucystineHMDB
L-(-)-CystineHMDB
L-Cysteine disulfideHMDB
L-CystinHMDB
[R-(R*,r*)]-3,3'-dithiobisHMDB
L CystineHMDB
Copper cystinateHMDB
L-CystineKEGG
Chemical FormulaC6H12N2O4S2
Average Molecular Weight240.3
Monoisotopic Molecular Weight240.023848262
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional NameL-cystine
CAS Registry Number56-89-3
SMILES
N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
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
InChI KeyLEVWYRKDKASIDU-IMJSIDKUSA-N
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
Experimental Properties
PropertyValueReference
Melting Point260.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 mg/mLNot Available
LogP-5.08CHMELIK,J ET AL. (1991)
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0950000000-a803bc05843192dd737d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0940000000-f82b905ef9e7c9e475522014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-49b9a52a8387d6d6f2722014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014j-1970000000-9576699202733d4fd7ed2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0950000000-a803bc05843192dd737d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9850000000-49b9a52a8387d6d6f2722017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-1970000000-9576699202733d4fd7ed2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0930000000-7cb336c3f272fd0fcd6b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0920000000-1c414573da4bbe4a66dd2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-9400000000-211575093fd775db5d542016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0076-9112000000-ee49e3b674a4f8bb9ecd2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0890000000-51a32ee40240e45646bc2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9700000000-4054924ddfb90f120e672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9100000000-085d45702e61de0f8e4d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9710000000-9321541af2ad89bd04782020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0090000000-041bfa55cb183f42f4542020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-000i-0190000000-3611e8b67151298421302020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0190000000-dbafdd64edad14af92812020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-000i-0290000000-6b80d283287249ba4b872020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-000i-0390000000-c091ce388dfcbd339e3f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0079-0690000000-c808ac294a0bc182c5eb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0079-0970000000-36297b29c4ef45c658e32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00dr-0940000000-a8c735a0f9082cfd7c7c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1920000000-9d55705325536cca5eb22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-00di-1910000000-cd18de2585913152e9072020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-00di-1900000000-3118609f8682bee472c62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-00di-2900000000-213ccc3c067486ff94442020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00di-3900000000-df68db23afd937a9a75d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-00di-4900000000-b46d26f57a194d2ff6482020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-00di-6900000000-5535cccb24de733cada32020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006w-2970000000-b80e0aef184b74ce7a362016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00re-4910000000-a09277c5a6bfc432eb792016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xu-9600000000-0518bfcaab380952c1232016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3590000000-aa667d3c092c5af3ae7f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-5910000000-122bd251359ca80b184c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9300000000-bbb14e684ff7c06e79162016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000x-9000000000-ae0f516d71e6a49fe52f2015-03-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Not Available2015-03-12View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified1124 uM details
Detected and Quantified1124 uM details
Detected and Quantified1124 uM details
Detected and Quantified1124 uM details
Detected and Quantified1081 uM details
Detected and Quantified1081 uM details
Detected and Quantified1081 uM details
HMDB IDHMDB0000192
DrugBank IDDB00138
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012672
KNApSAcK IDC00001352
Chemspider ID60997
KEGG Compound IDC00491
BioCyc IDNot Available
BiGG ID35134
Wikipedia LinkCystine
METLIN ID5207
PubChem Compound67678
PDB IDNot Available
ChEBI ID16283
References
Synthesis ReferenceGrossi, 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)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  4. Fooddata+, The Technical University of Denmark (DTU) [Link]