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L-Cysteine (PC000239)

Record Information
Version1.0
Creation date2015-10-09 22:29:23 UTC
Update date2017-01-19 02:36:17 UTC
FoodComEx IDPC000239
FoodDB RecordFDB012678
Chemical Information
NameL-Cysteine
DescriptionL-Cysteine, also known as C or e 920, 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. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine is a very strong basic compound (based on its pKa). L-Cysteine exists in all living species, ranging from bacteria to humans. Within humans, L-cysteine participates in a number of enzymatic reactions. In particular, L-cysteine can be converted into 3-sulfinoalanine; which is mediated by the enzyme cysteine dioxygenase type 1. In addition, L-cysteine can be converted into hydrogen sulfide and pyruvic acid through the action of the enzyme cystathionine gamma-lyase. In humans, L-cysteine is involved in cysteine metabolism. L-Cysteine is a sulfury tasting compound. Outside of the human body, L-Cysteine is found, on average, in the highest concentration within a few different foods, such as sunflowers, soy beans, and watermelons and in a lower concentration in common wheats, dates, and beers. L-Cysteine has also been detected, but not quantified in, several different foods, such as oyster mushrooms, salmonberries, rapes, safflowers, and cupuaçus. This could make L-cysteine a potential biomarker for the consumption of these foods. L-Cysteine is a potentially toxic compound. An optically active form of cysteine having L-configuration.
CAS Number52-90-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-2-Amino-3-mercaptopropionic acidbiospider
(2R)-2-Amino-3-mercaptopropanoatebiospider
(2R)-2-Amino-3-mercaptopropanoic acidbiospider
(2R)-2-Amino-3-sulfanylpropanoatebiospider
(2R)-2-Amino-3-sulfanylpropanoic acidbiospider
(2R)-2-amino-3-SulphanylpropanoateGenerator
(2R)-2-amino-3-Sulphanylpropanoic acidGenerator
(R)-(+)-Cysteinebiospider
(R)-2-Amino-3-mercapto-propanoatebiospider
(R)-2-Amino-3-mercapto-propanoic acidbiospider
(R)-2-Amino-3-mercaptopropanoatebiospider
(R)-2-Amino-3-mercaptopropanoic acidbiospider
(R)-2-Amino-3-mercaptopropionic acidbiospider
(R)-Cysteinebiospider
α-amino-β-Thiolpropionic acidbiospider
β-Mercaptoalaninebiospider
2-Amino-3-mercapto-, (R)-biospider
2-Amino-3-mercaptopropanoatebiospider
2-Amino-3-mercaptopropanoic acidbiospider
2-Amino-3-mercaptopropanoic acid, (R)-biospider
2-Amino-3-mercaptopropionatebiospider
2-Amino-3-mercaptopropionic acidbiospider
3-Mercapto-L-Alaninebiospider
alpha-Amino-beta-mercaptopropanoic acid, L-biospider
alpha-Amino-beta-mercaptopropionic acid, L-biospider
alpha-Amino-beta-thiolpropionic acidbiospider
alpha-Amino-beta-thiolpropionic acid, L-biospider
b-Mercaptoalaninebiospider
beta-Mercaptoalaninebiospider
beta-Mercaptoalanine, L-biospider
CarbocysteineHMDB
CisteinaHMDB
CisteinumHMDB
CYSbiospider
CysteinHMDB
Cysteinebiospider
Cysteine, INN; L-formdb_source
CysteinumHMDB
e920ChEBI
Ecolan (TN)biospider
FREE cysteineChEBI
Half-cystineHMDB
L CysteineHMDB
L-(+)-Cysteinebiospider
L-2-Amino-3-mercaptopropanoatebiospider
L-2-Amino-3-mercaptopropanoic acidbiospider
L-2-amino-3-MercaptopropionateGenerator
L-2-Amino-3-mercaptopropionic acidbiospider
L-Alanine, 3-mercapto-biospider
L-CYSbiospider
L-CysteinChEBI
L-Cysteinebiospider
L-ZysteinChEBI
PolycysteineHMDB
Propanoic Acid, 2-amino-3-mercapto-, (R)-biospider
Thioserinebiospider
Chemical FormulaC3H7NO2S
IUPAC name(2R)-2-amino-3-sulfanylpropanoic acid
InChI IdentifierInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyXUJNEKJLAYXESH-REOHCLBHSA-N
Isomeric SMILESN[C@@H](CS)C(O)=O
Average Molecular Weight121.158
Monoisotopic Molecular Weight121.019749163
Chemical Taxonomy
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
  • L-alpha-amino acid
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-2.49HANSCH,C ET AL. (1995)
Experimental Water Solubility277 mg/mL at 25 oCBEILSTEIN
Melting PointMp 178° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 400 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci G143
AKSci J93374
Glentham GM3760
MetaSci HMDB0000574
Sigma-Aldrich HMDB0000574
Toronto Research Chemicals C995000