CAS 52-90-4|L-cysteine|(2R)-2-amino-3-sulfanylpropanoic acid|Free Cysteine|b-Mercaptoalanine|L-2-Amino-3-mercaptopropionic acid|Thioserine|Cystein|(R)-2-amino-3-mercaptopropanoic acid|(R)-2-Amino-3-...

InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

XUJNEKJLAYXESH-REOHCLBHSA-N

LogD (pH = 7.4)

-2.87

LogD (pH = 5.5)

-2.79

Log P

-2.79

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

2.35

Polar Surface Area

63.32

Polarizability

11.41

Molar Refractivity

28.22

LOG S

-0.23

(2R)-2-amino-3-sulfanylpropanoic acid

Free CysteineL-CysteineCysteinThioserine(R)-2-amino-3-mercaptopropanoic acid(R)-2-Amino-3-mercaptopropanoic acidb-MercaptoalanineL-2-Amino-3-mercaptopropionic acidCys2-Amino-3-mercaptopropionic acid3-mercapto-L-AlaninecarbocysteineHalf-cystine(R)-CysteineL-CysL-(+)-CysteineL-CYSTEINE FREE BASEβ-Mercapto-L-alanineL-CysteineL-半胱氨酸(R)-2-Amino-3-mercaptopropionic acid(R)-2-氨基-3-巯基丙酸(2R)-2-Amino-3-mercaptopropanoic acid(2R)-2-Amino-3-mercaptopropionic acid2-Amino-3-sulfhydrylpropanoic acid(2R)-2-Amino-3-sulphanylpropanoic acidCysteineE 920β-MercaptoalanineCysteineNSC 8746L半胱氨酸H-Cys-OHL-Zystein(R)-2-amino-3-mercaptopropanoic acid(2R)-2-amino-3-sulfanylpropanoic acidE920L-CysteineFREE CYSTEINECYSTEINEL-CysteinE-920(2R)-2-amino-3-mercaptopropanoic acidL-2-Amino-3-mercaptopropionic acidCL-cysteineCysE 920

IUPAC Traditional name

Unique Ingredient Identifier

PubMed Citation Links

BRENDA Ligand Database

MetaboLights Database

Drug Central Database

VirtualMetabolicHuman Database

EnzymePortal Database

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DB00151

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]

• Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. Pubmed

• Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. 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)

Names and Identifiers

IUPAC name

(2R)-2-amino-3-sulfanylpropanoic acid

Synonyms

IUPAC Traditional name

L-cysteine

References

PubChem Literature

From Data Sources

• Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. Pubmed

• Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. 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)

Bioactivity

PubChem BioAssay

Molecule Details

DrugBank

DB00151

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

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]

DB04443

Drug information: experimental

MP Biomedicals

02101444

Free Base
Crystalline

02194646

Free Base
Cell Culture Reagent
Crystalline

Sigma Aldrich

168149

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

W326305

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

C7352

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.

30089

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

30090

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

95437

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

05-7460

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

C5360

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

TRC

C995000

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

ChEBI

CHEBI:17561

An optically active form of cysteine having L-configuration.

Ni: ≤5 mg/kg

Mo: ≤5 mg/kg

Pb: ≤5 mg/kg

Cr: ≤5 mg/kg

K: ≤50 mg/kg

Mg: ≤5 mg/kg

Co: ≤5 mg/kg

Sr: ≤5 mg/kg

Bi: ≤5 mg/kg

Cu: ≤5 mg/kg

Mn: ≤5 mg/kg

Zn: ≤5 mg/kg

German water hazard class

GHS Hazard statements

Personal Protective Equipment

GHS Precautionary statements

Molecule

ID:37