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56-89-3 molecular structure
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(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

ChemBase ID: 24
Molecular Formular: C6H12N2O4S2
Molecular Mass: 240.30048
Monoisotopic Mass: 240.02384887
SMILES and InChIs

SMILES:
S(SC[C@H](N)C(=O)O)C[C@H](N)C(=O)O
Canonical SMILES:
N[C@H](C(=O)O)CSSC[C@@H](C(=O)O)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
InChIKey:
LEVWYRKDKASIDU-IMJSIDKUSA-N

Cite this record

CBID:24 http://www.chembase.cn/molecule-24.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
IUPAC Traditional name
L-cystine
Synonyms
(-)-Cystine
Cysteine disulfide
Cystine acid
L-alpha-Diamino-beta-dithiolactic acid
L-Dicysteine
Dicysteine
3,3'-Dithiobis (2-aminopropanoic acid)
Cystein disulfide
L-Cystine
(R,R)-3,3′-Dithiobis(2-aminopropionicacid)
L-Cystine
3,3'-Dithiobis(2-aminopropanoic Acid)
Bis(β-amino-β-carboxyethyl) Disulfide
Cystine Αcid
3,3'-Dithiobis-L-Alanine
L-Cysteine Disulfide
L-Cystin
NSC 13203
Oxidized L-cysteine
[R-(R*,R*)]-3,3'-Dithiobis[2-aminopropanoic Acid]
l-Cystine
β,β'-Diamino-β,β'-dicarboxydiethyl Disulfide
β,β'-Dithiodialanine
H-(Cys)2-OH
(-)-3,3'-Dithiobis(2-aminopropionic acid)
(R,R)-3,3′-二硫双(2-氨基丙酸)
L-胱氨酸
CAS Number
56-89-3
EC Number
200-296-3
MDL Number
MFCD00064228
Beilstein Number
1728094
Merck Index
142782
PubChem SID
160963487
46506670
24892973
24893101
24892581
24858224
PubChem CID
67678
E Number
E921

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.5564231  H Acceptors
H Donor LogD (pH = 5.5) -5.897319 
LogD (pH = 7.4) -5.9155164  Log P -5.897688 
Molar Refractivity 54.8718 cm3 Polarizability 22.177225 Å3
Polar Surface Area 126.64 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.16  LOG S -1.16 
Solubility (Water) 1.68e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble0.2 M at 20 °C, clear, colorless expand Show data source
1 M HCl: soluble100 mg/mL expand Show data source
Soluble expand Show data source
Apperance
crystalline expand Show data source
powder expand Show data source
Melting Point
>240 °C (dec.)(lit.) expand Show data source
>240°C dec. expand Show data source
260 - 261°C expand Show data source
Density
1.68 expand Show data source
Optical Rotation
[α]20/D -217.8°, c = 1 in 1 M HCl expand Show data source
[α]20/D -219±5°, c = 1% in 1 M HCl expand Show data source
-219 (c=1 in 1N HCl) expand Show data source
Hydrophobicity(logP)
-5.5 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
HA2690000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98% (TLC) expand Show data source
≥98.5% expand Show data source
≥99.0% expand Show data source
≥99.5% (T) expand Show data source
97% expand Show data source
98.5-101.0% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.05% (as SO4) expand Show data source
Impurities
≤0.3% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤10 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤500 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.05% loss on drying, 20 °C (HV) expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
Product Line
BioUltra expand Show data source
abs.
absorption0.2M/316 nm, 1 M HCl cut-off expand Show data source
Linear Formula
[-SCH2CH(NH2)CO2H]2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00138 external link
Item Information
Drug Groups approved; nutraceutical
Description 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. [PubChem]
Indication It has been claimed that L-cysteine has anti-inflammatory properties, that it can protect against various toxins, and that it might be helpful in osteoarthritis and rheumatoid arthritis. More research will have to be done before L-cysteine can be indicated for any of these conditions. Research to date has mostly been in animal models.
Pharmacology 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.
Toxicity With typical doses of 1 to 1.5 grams daily, the most commonly reported side effects have been gastrointestinal, such as nausea. There are rare reports of cystine renal stone formation, Single injections of L-cysteine (0.6-1.5 g/kg) into 4-day-old pups resulted in massive damage to cortical neurons, permanent retinal dystrophy, atrophy of the brain and hyperactivity.
Affected Organisms
Humans and other mammals
External Links
PDRhealth
MP Biomedicals - 02101454 external link
Purity: 99%
White crystals
MP Biomedicals - 02194649 external link
Cell Culture Reagent Purity: 99% White crystals
MP Biomedicals - 05202117 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - C7602 external link
包装
10 mg in autosmp vl
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - C5735 external link
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - C8755 external link
包装
100, 500 g in poly bottle
Sigma Aldrich - C122009 external link
Packaging
2.5 g in glass bottle
Sigma Aldrich - 30199 external link
Other Notes
Certain malignant cell lines require cystine or cysteine in the culture medium1; Growth requirement of various microorganisms2
Sigma Aldrich - 49603 external link
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - C997860 external link
L-Cystine is a non-essential amino acid for human development. L-Cystine is formed by the dimerization of two cysteines through the sulfur.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Fahey, R.C., et al.: J. Mol. Evol., 10, 155 (1977)
  • • Kao, P., et al.: J. Biol.Chem., 261, 8085 ( 1986), Nicke, A., et al.: J. Biol. Chem., 278, 3137 (1977)
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PATENTS

PATENTS

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INTERNET

INTERNET

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