Record Information
Version1.0
Creation date2010-04-08 22:10:14 UTC
Update date2019-11-26 03:07:05 UTC
Primary IDFDB012563
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Cystine
DescriptionFlavouring ingredient; dietary supplement Cystine 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. Cystine is found in high concentrations in the cells of the immune system, skeletal and connective tissues, skin, digestive enzymes, and in hair. Hair and skin are 10-14% cystine. Cystine is the preferred form of cysteine for the synthesis of glutathione in cells involved in the immune function including macrophages and astrocytes. Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand. (http://en.wikipedia.org/wiki/Cystine); Cystine is the amino acid formed by the oxidation of cysteine molecules to give a disulfide bond. This organosulfur compound has the formula (SCH2CH(NH2)CO2H)2. It is a colorless solid, and melts at 247-249 °C. It was discovered in 1810 by William Hyde Wollaston but was not recognized as being derived of proteins until it was isolated from the horn of a cow in 1899. 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. Human hair contains approximately 5% cystine by mass.; L-Cystine is a covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. Cystine is a chemical substance which naturally occurs as a deposit in the urine, and can form a calculus (hard mineral formation) when deposited in the kidney. The compound produced when two cysteine molecules linked by a disulfide (S-S) bond. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc.
CAS Number56-89-3
Structure
Thumb
Synonyms
SynonymSource
3,3'-Dithiobis(2-aminopropanoic acid)ChEBI
alpha-Diamino-beta-dithiolactic acidChEBI
CistinaChEBI
CystinChEBI
DicysteineChEBI
ZystinChEBI
3,3'-Dithiobis(2-aminopropanoate)Generator
a-Diamino-b-dithiolactateGenerator
a-Diamino-b-dithiolactic acidGenerator
alpha-Diamino-beta-dithiolactateGenerator
Α-diamino-β-dithiolactateGenerator
Α-diamino-β-dithiolactic acidGenerator
Copper cystinateMeSH
CystineMeSH
L-CystineMeSH
L CystineMeSH
(-)-CystineHMDB
(2R,2'R)-3,3'-disulfanediylbis(2-aminopropanoic acid)biospider
(R-(R*,R*))-3,3'-Dithiobisbiospider
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)Generator
(R-(R*,R*))-3,3'-Dithiobis(2-aminopropanoic acid)biospider
(R,R)-3,3'-Dithiobis(2-aminopropanoate)Generator
(R,R)-3,3'-dithiobis(2-aminopropanoic acid)biospider
(R,R)-3,3'-Dithiobis(2-aminopropionicacid)biospider
[R-(R*,R*)]-3,3'-Dithiobisbiospider
α-diamino-β-dithiolactic acidbiospider
β,β'-dithiobisalaninebiospider
β,β'-dithiodialaninebiospider
1-Cystinebiospider
2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoatebiospider
2-amino-3-(2-amino-2-Carboxy-ethyl)disulfanyl-propanoic acidHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoatebiospider
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acidbiospider
3, 3'-Dithiobis(2-aminopropanoic acid)biospider
3,3'-Dithiobisbiospider
3,3'-dithiobis-L-Alaninebiospider
3,3'-Dithiobis(2-aminopropanoic acid), (R-(R*,R*))-biospider
3,3'-Dithiobis(2-aminopropionic acid)biospider
3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoatebiospider
3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acidbiospider
3,3'-DithiodialanineHMDB
Alanine, 3, 3'-dithiobis-biospider
B,b'-diamino-b,b'-dicarboxydiethyl disulfidebiospider
B,b'-dithiodialaninebiospider
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfideGenerator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphideGenerator
b,Beta'-dithiodialanineGenerator
Beta,beta'-diamino-beta,beta'-dicarboxydiethyl disulfidebiospider
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphideGenerator
Beta,beta'-diamino-beta,beta'-dicarboxydiethyldisulfidebiospider
Beta,beta'-dithioalanine, l-biospider
Beta,beta'-dithiobisalaninebiospider
Beta,beta'-dithiodialaninebiospider
Bis(β-amino-β-carboxyethyl) disulfidebiospider
Bis(β-amino-β-carboxyethyl)disulfidebiospider
Bis(b-amino-b-carboxyethyl) disulfidebiospider
Bis(b-amino-b-carboxyethyl) disulphideGenerator
Bis(b-amino-beta-carboxyethyl) disulfidebiospider
Bis(beta-amino-beta-carboxyethyl) disulfidebiospider
Bis(beta-amino-beta-carboxyethyl) disulphideGenerator
Bis(beta-amino-beta-carboxyethyl)disulfidebiospider
Bis(β-amino-β-carboxyethyl) disulfideGenerator
Bis(β-amino-β-carboxyethyl) disulphideGenerator
Cysteine disulfideHMDB
Cystin (van)biospider
Cystine (l)-biospider
Cystine (usan/inn)biospider
Cystine (van)biospider
Cystine [usan]biospider
Cystine acidHMDB
Cystine d-formbiospider
Cystine, 9CI, USAN; L-formdb_source
Cystine, d-biospider
Cystine, L- (8CI)biospider
Cystine,dbiospider
D(+)-3,3'-Dithiobis(2-aminopropanoatebiospider
D(+)-3,3'-Dithiobis(2-aminopropanoic acidbiospider
e921ChEBI
Gelucystinebiospider
Gelucystine (l form)biospider
L-(-)-CystineHMDB
L-3,3'-dithiodialaninebiospider
L-a-Diamino-b-dithiolactateGenerator
L-a-Diamino-b-dithiolactic acidGenerator
L-Alanine, 3,3'-dithiobis-biospider
L-alpha-Diamino-beta-dithiolactateGenerator
L-alpha-diamino-beta-dithiolactic acidbiospider
L-cysteine disulfidebiospider
L-cystinbiospider
L-Cystine (9CI)biospider
L-dicysteinebiospider
L-α-diamino-β-dithiolactateGenerator
L-α-diamino-β-dithiolactic acidGenerator
Oxidized L-cysteineChEBI
Propanoic acid, 3,3'-dithiobis(2-amino-, (R-(R*,R*))-biospider
β,beta'-diamino-β,beta'-dicarboxydiethyl disulfideGenerator
β,beta'-diamino-β,beta'-dicarboxydiethyl disulphideGenerator
β,beta'-dithiodialanineGenerator
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
Polarizability22.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H12N2O4S2
IUPAC name2-amino-3-[(2-amino-2-carboxyethyl)disulfanyl]propanoic acid
InChI IdentifierInChI=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)
InChI KeyLEVWYRKDKASIDU-UHFFFAOYSA-N
Isomeric SMILESNC(CSSCC(N)C(O)=O)C(O)=O
Average Molecular Weight240.3
Monoisotopic Molecular Weight240.023848262
Classification
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
  • Dicarboxylic acid or derivatives
  • Organic disulfide
  • Dialkyldisulfide
  • Amino acid
  • Sulfenyl compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 29.99%; H 5.03%; N 11.66%; O 26.63%; S 26.69%DFC
Melting PointMp 258-261 dec. (sealed tube)DFC
Boiling PointNot Available
Experimental Water Solubility0.19 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-5.08CHMELIK,J ET AL. (1991)
Experimental pKapKa4 9.85 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -232 (c, 1 in 5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot 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
ChemSpider ID60997
ChEMBL IDCHEMBL590540
KEGG Compound IDC00491
Pubchem Compound ID67678
Pubchem Substance IDNot Available
ChEBI ID16283
Phenol-Explorer IDNot Available
DrugBank IDDB00138
HMDB IDHMDB00192
CRC / DFC (Dictionary of Food Compounds) IDHHZ63-J:HHZ66-M
EAFUS ID816
Dr. Duke IDCYSTINE
BIGG ID35134
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCystine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
adjuvant60809 Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.DUKE
anti homocystinuricDUKE
Enzymes
NameGene NameUniProt ID
Cystathionine gamma-lyaseCTHP32929
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).