Canmetcon
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Identification
YMDB IDYMDB00913
NameD-Cysteine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCysteine (abbreviated as Cys or C) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. D-isomers are used as carbon, nitrogen, and energy source. Cysteine is unique among the twenty common amino acids because it contains a thiol group.
Structure
Thumb
Synonyms
  • D-Amino-3-mercaptopropionate
  • D-Amino-3-mercaptopropionic acid
  • (2S)-2-Amino-3-mercaptopropanoic acid
  • (2S)-2-Amino-3-sulfanylpropanoic acid
  • (S)-2-Amino-3-mercaptopropanoic acid
  • D-Cystein
  • D-Zystein
  • DCY
  • (2S)-2-Amino-3-mercaptopropanoate
  • (2S)-2-Amino-3-sulfanylpropanoate
  • (2S)-2-Amino-3-sulphanylpropanoate
  • (2S)-2-Amino-3-sulphanylpropanoic acid
  • (S)-2-Amino-3-mercaptopropanoate
  • Cysteine
  • Half cystine
  • Cysteine hydrochloride
  • Half-cystine
  • L-Cysteine
  • L Cysteine
  • Zinc cysteinate
CAS number921-01-7
WeightAverage: 121.158
Monoisotopic: 121.019749163
InChI KeyXUJNEKJLAYXESH-UWTATZPHSA-N
InChIInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1
IUPAC Name(2S)-2-amino-3-sulfanylpropanoic acid
Traditional IUPAC NameL cysteine
Chemical FormulaC3H7NO2S
SMILES[H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])S[H]
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
  • D-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
Physical Properties
StateSolid
Charge0
Melting point220 °C
Experimental Properties
PropertyValueReference
Water Solubility277 mg/mL at 25 oC [BEILSTEIN]PhysProp
LogP-2.49 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP-2.6ALOGPS
logP-2.8ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.22 m³·mol⁻¹ChemAxon
Polarizability11.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Abe, T., Hashimoto, Y., Hosaka, H., Tomita-Yokotani, K., Kobayashi, M. (2008). "Discovery of amide (peptide) bond synthetic activity in Acyl-CoA synthetase." J Biol Chem 283:11312-11321.18305111
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16375
HMDB IDHMDB03417
Pubchem Compound ID92851
Kegg IDC00793
ChemSpider ID83819
FOODB IDFDB023168
WikipediaCarbon_dioxide
BioCyc IDD-CYSTEINE

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:
HPA3
Uniprot ID:
P39979
Molecular weight:
20698.5
Reactions
acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid