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52-90-4 molecular structure
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(2R)-2-amino-3-sulfanylpropanoic acid

ChemBase ID: 37
Molecular Formular: C3H7NO2S
Molecular Mass: 121.15818
Monoisotopic Mass: 121.01974947
SMILES and InChIs

SMILES:
SC[C@H](N)C(=O)O
Canonical SMILES:
N[C@H](C(=O)O)CS
InChI:
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChIKey:
XUJNEKJLAYXESH-REOHCLBHSA-N

Cite this record

CBID:37 http://www.chembase.cn/molecule-37.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-amino-3-sulfanylpropanoic acid
IUPAC Traditional name
L-cysteine
Synonyms
L-2-Amino-3-mercaptopropionic acid
3-mercapto-L-Alanine
L-Cys
L-(+)-Cysteine
Half-cystine
Thioserine
Cystein
Cys
carbocysteine
b-Mercaptoalanine
2-Amino-3-mercaptopropionic acid
(R)-Cysteine
(R)-2-Amino-3-mercaptopropanoic acid
L-Cysteine
(2R)-2-Amino-3-sulphanylpropanoic acid
(2R)-2-Amino-3-mercaptopropionic acid
(2R)-2-Amino-3-mercaptopropanoic acid
β-Mercapto-L-alanine
Free Cysteine
(R)-2-amino-3-mercaptopropanoic acid
2-Amino-3-sulfhydrylpropanoic acid
Cysteine
(R)-2-Amino-3-mercaptopropionic acid
L-Cysteine
Cysteine
E 920
NSC 8746
β-Mercaptoalanine
L-CYSTEINE FREE BASE
H-Cys-OH
(R)-2-氨基-3-巯基丙酸
L-半胱氨酸
L半胱氨酸
CAS Number
52-90-4
EC Number
200-158-2
MDL Number
MFCD00064306
Beilstein Number
1721408
Merck Index
142781
PubChem SID
24892959
160963500
24858110
46506553
24892777
24901592
24850236
PubChem CID
5862
CHEBI ID
15356
CHEMBL
54943
Chemspider ID
574
FEMA ID
3263
KEGG ID
D00026
Unique Ingredient Identifier
K848JZ4886
Wikipedia Title
Cysteine
Flavis Number
17.033
E Number
E920

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.3459952  H Acceptors
H Donor LogD (pH = 5.5) -2.7920592 
LogD (pH = 7.4) -2.8006835  Log P -2.7921333 
Molar Refractivity 28.2236 cm3 Polarizability 11.415023 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.57  LOG S -0.72 
Solubility (Water) 2.31e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble1 M at 20 °C, clear, colorless expand Show data source
1.5g/100g ethanol 19 degC expand Show data source
277 mg/mL at 25 oC [BEILSTEIN] expand Show data source
H2O: soluble25 mg/mL expand Show data source
soluble in water expand Show data source
Apperance
white crystals or powder expand Show data source
Melting Point
220 °C (dec.)(lit.) expand Show data source
240 °C decomp. expand Show data source
240(dec.)°C expand Show data source
ca 220°C dec. expand Show data source
decomposes 175-178 °C expand Show data source
Optical Rotation
[α]20/D +6.5±1.5°, c = 2 in 5 M HCl expand Show data source
[α]20/D +7.6±0.5°, c = 5% in 5 M HCl expand Show data source
[α]20/D +8.0±0.5°, c = 5% in 5 M HCl expand Show data source
[α]26/D +8.0 to +9.5°, c = 2 in 5 M HCl expand Show data source
+7.9 (c=5 in 5N HCl) expand Show data source
+9.4° (H2O, c = 1.3) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 1.5 expand Show data source
λ: 280 nm Amax: 0.2 expand Show data source
Hydrophobicity(logP)
-2.6 expand Show data source
Storage Condition
Room Temperature (15-30°C), Desiccate, Store Under Nitrogen expand Show data source
Storage Warning
Air Sensitive expand Show data source
Harmful/Irritant/Air Sensitive/Store under Argon expand Show data source
RTECS
HA1600000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
22 expand Show data source
R:22-36/37/38 expand Show data source
Safety Statements
36/37 expand Show data source
S:25-26-36/37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
GHS Precautionary statements
P264-P270-P301+P312-P330-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
20-25°C expand Show data source
2-8°C expand Show data source
Purity
≥97% expand Show data source
≥98% expand Show data source
≥98.5% expand Show data source
≥98.5% (RT) expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
NI expand Show data source
PharmaGrade expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Optical Purity
ee: 96% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
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
≤0.1% (as SO4) expand Show data source
Impurities
≤0.5% 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: ≤5 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: ≤100 mg/kg expand Show data source
NH4+: ≤500 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-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤50 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
≤0.1% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
1 M in 1 M HCl expand Show data source
Product Line
BioReagent expand Show data source
BioUltra expand Show data source
Linear Formula
HSCH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00151 external link
Item Information
Drug Groups approved; nutraceutical
Description A thiol-containing non-essential amino acid that is oxidized to form cystine. [PubChem]
Indication For the prevention of liver damage and kidney damage associated with overdoses of acetaminophen
Pharmacology Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine may at some point be recognized as an essential or conditionally essential amino acid.
Affected Organisms
Humans and other mammals
References
Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. [Pubmed]
Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. [Pubmed]
External Links
Wikipedia
DrugBank - DB04443 external link
Drug information: experimental
MP Biomedicals - 02101444 external link
Free Base
Crystalline
MP Biomedicals - 02194646 external link
Free Base
Cell Culture Reagent
Crystalline
Sigma Aldrich - 168149 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
General description
Naturally occurring non-essential amino acid.
Packaging
2.5 g in glass bottle
2.5 kg in poly bottle
25, 100, 500 g in poly bottle
Sigma Aldrich - C7352 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Other Notes
L-Cysteine is used to supplement cell culture media. This product is a non-animal source amino acid useful for serum-free media formulations intended for biomanufacturing applications.
Packaging
10 mg in autosmp vl
General description
L-Cysteine is a proteinogenic amino acid incorporated into proteins as directed by the genetic code. The thiol-side chain participates in a variety of oxidation/reduction reactions within the cell. The side chain participates in the formation of β bonds that modulate the secondary and ternary structure of proteins. Cysteine is essential and limiting for the formation of glutathione, an important antioxidant, within the cell.
Sigma Aldrich - 30090 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Sigma Aldrich - 30089 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Sigma Aldrich - 05-7460 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Sigma Aldrich - C5360 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Non-animal source L-cysteine is used as a cell culture media component for the commercial biomanufacture of therapeutic recombinant proteins and monoclonal antibodies.
Quality
Manufactured and Packaged under cGMP
Sigma Aldrich - 95437 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.
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
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
Sigma Aldrich - W326305 external link
Biochem/physiol Actions
NMDA glutamatergic receptor agonist.
Packaging
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum
Toronto Research Chemicals - C995000 external link
L-Cysteine is a non-essential amino acid that can be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. L-Cysteine is commonly used as a precursor in the food and pharmaceutical industr

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. Pubmed
  • • Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. Pubmed
  • • Pecivova, P. et al.: J. Sci. Food Agric., 90, 1681 (2010)
  • • Hui, N. et al.: Meat Sci. Appl., 74 (2010)
  • • Kiviharju, K. et al.: J. Biotechnol., 117, 299 (2010)
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PATENTS

PATENTS

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INTERNET

INTERNET

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