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

• ChemBase ID: 37
• Molecular Formular: C3H7NO2S
• Molecular Mass: 121.15818
• Monoisotopic Mass: 121.01974947
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-sulfanylpropanoic acid
• IUPAC Traditional name: L-cysteine
• Synonyms: Cysteine; E 920; NSC 8746; β-Mercaptoalanine; H-Cys-OH; (R)-2-amino-3-mercaptopropanoic acid; 2-Amino-3-sulfhydrylpropanoic acid; Cysteine; (R)-2-Amino-3-mercaptopropionic acid; L-Cysteine; β-Mercapto-L-alanine; L-CYSTEINE FREE BASE; (2R)-2-Amino-3-sulphanylpropanoic acid; (2R)-2-Amino-3-mercaptopropionic acid; (2R)-2-Amino-3-mercaptopropanoic acid; 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; Free Cysteine; L半胱氨酸; (R)-2-氨基-3-巯基丙酸; L-半胱氨酸

Database IDs

• CAS Number: 52-90-4
• EC Number: 200-158-2
• MDL Number: MFCD00064306
• Beilstein Number: 1721408
• Merck Index: 142781
• PubChem SID: 160963500; 46506553; 24892777; 24858110; 24850236; 24892959; 24901592
• 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

JChem

• Acid pKa: 2.3459952
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.7920592
• LogD (pH = 7.4): -2.8006835
• Log P: -2.7921333
• Molar Refractivity: 28.2236 cm^3
• Polarizability: 11.415023 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.57
• LOG S: -0.72
• Solubility (Water): 2.31e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble1 M at 20 °C, clear, colorless; 1.5g/100g ethanol 19 degC; 277 mg/mL at 25 oC [BEILSTEIN]; H2O: soluble25 mg/mL; soluble in water
• Apperance: white crystals or powder
• Melting Point: 220 °C (dec.)(lit.); 240 °C decomp.; 240(dec.)°C; ca 220°C dec.; decomposes 175-178 °C
• Optical Rotation: [α]20/D +6.5±1.5°, c = 2 in 5 M HCl; [α]20/D +7.6±0.5°, c = 5% in 5 M HCl; [α]20/D +8.0±0.5°, c = 5% in 5 M HCl; [α]26/D +8.0 to +9.5°, c = 2 in 5 M HCl; +7.9 (c=5 in 5N HCl); +9.4° (H₂O, c = 1.3)
• Absorption Wavelength: λ: 260 nm Amax: 1.5; λ: 280 nm Amax: 0.2
• Hydrophobicity(logP): -2.6

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: Air Sensitive; Harmful/Irritant/Air Sensitive/Store under Argon
• RTECS: HA1600000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; R:22-36/37/38
• Safety Statements: 36/37; S:25-26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 20-25°C; 2-8°C

Product Information

• Purity: ≥97%; ≥98%; ≥98.5%; ≥98.5% (RT); 97%; 98%; 98+%
• Grade: certified reference material; EP; NI; PharmaGrade; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 96% (GLC)
• Suitability: suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.05% (as SO4); ≤0.1% (as SO4)
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤100 mg/kg; NH4+: ≤500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 1 M in 1 M HCl
• Product Line: BioReagent; BioUltra
• Linear Formula: HSCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02101444

Free Base
Crystalline

MP Biomedicals - 02194646

Free Base
Cell Culture Reagent
Crystalline

DrugBank - DB04443

Drug information: experimental

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: 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

Sigma Aldrich - 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.

Sigma Aldrich - 30089

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

Sigma Aldrich - 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

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

Sigma Aldrich - 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

Sigma Aldrich - 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

Sigma Aldrich - 30090

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

Sigma Aldrich - 05-7460

Biochem/physiol Actions
NMDA glutamatergic receptor agonist.

Toronto Research Chemicals - 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

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
• 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)