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Identification
YMDB IDYMDB00046
NameL-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. It is classified as a nonpolar amino acid. The side chain on cysteine is thiol, which is considered nonpolar. The thiol side chain often participates in enzymatic reactions, serving as a nucleophile. The thiol is susceptible to oxidization to give the disulfide derivative cystine, which serves an important structural role in many proteins. Cysteine biosynthesis starts from serine, which is converted to O-acetylserine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate. Cysteine, mainly the L-enantiomer, is a precursor in the food, pharmaceutical, and personal care industries. One of the largest applications is the production of flavors. For example, the reaction of cysteine with sugars in a Maillard reaction yields meat flavors. L-cysteine is also used as a processing aid for baking.
Structure
Thumb
Synonyms
  • (+)-2-Amino-3-mercaptopropionic acid
  • (2R)-2-amino-3-mercaptopropanoate
  • (2R)-2-amino-3-mercaptopropanoic acid
  • (2R)-2-amino-3-sulfanylpropanoate
  • (2R)-2-amino-3-sulfanylpropanoic acid
  • (2R)-2-amino-3-Sulphanylpropanoate
  • (2R)-2-amino-3-Sulphanylpropanoic acid
  • (R)-(+)-cysteine
  • (R)-2-amino-3-mercapto-Propanoate
  • (R)-2-amino-3-mercapto-Propanoic acid
  • (R)-2-Amino-3-mercaptopropanoate
  • (R)-2-Amino-3-mercaptopropanoic acid
  • (R)-cysteine
  • 2-Amino-3-mercaptopropanoate
  • 2-Amino-3-mercaptopropanoic acid
  • 2-Amino-3-mercaptopropionate
  • 2-Amino-3-mercaptopropionic acid
  • 3-mercapto-L-Alanine
  • acetylcysteine
  • alpha-amino-beta-thiolpropionic acid
  • B-mercaptoalanine
  • beta-mercaptoalanine
  • C
  • Carbocysteine
  • Cisteina
  • Cisteinum
  • Cys
  • Cystein
  • Cysteine
  • Cysteine hydrochloride
  • Cysteinum
  • e 920
  • e-920
  • e920
  • Free cysteine
  • Half cystine
  • Half-cystine
  • L cysteine
  • L-(+)-cysteine
  • L-2-Amino-3-mercaptopropanoate
  • L-2-Amino-3-mercaptopropanoic acid
  • L-2-amino-3-Mercaptopropionate
  • L-2-Amino-3-mercaptopropionic acid
  • L-cystein
  • L-cysteine
  • L-Zystein
  • Polycysteine
  • Thioserine
  • Zinc cysteinate
  • Ecolan
CAS number52-90-4
WeightAverage: 121.158
Monoisotopic: 121.019749163
InChI KeyXUJNEKJLAYXESH-REOHCLBHSA-N
InChIInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
IUPAC Name(2R)-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
Polarizability11.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
SulfuryFDB012678
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Taurine and hypotaurine metabolismec00430 Map00430
Thiamine metabolismec00730 Map00730
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Glutathione + L-CysteineL-cysteinylglycine + Gamma-Glutamylcysteine
L-cysteinylglycine + waterGlycine + L-Cysteine
D-4'-Phosphopantothenate + Cytidine triphosphate + L-CysteineCytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
Hydrogen sulfide + O-acetyl-L-serineL-Cysteine + Acetic acid + hydron
L-Cysteinehydron + Hydrogen sulfide + 2-Aminoacrylic acid
KEGG Reactions
O-Succinyl-L-homoserine + L-CysteineL-Cystathionine + hydron + Succinic acid
D-4'-Phosphopantothenate + L-Cysteine + Cytidine triphosphatePyrophosphate + 4-Phosphopantothenoylcysteine + Cytidine monophosphate + hydron
Glycine + alpha-D-ribose 5-phosphate + hydron + L-Cysteine + O-Acetyl-L-homoserinePyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
Glycine + hydron + L-Cysteine + Xylulose 5-phosphate + O-Acetyl-L-homoserinePyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ono, B., Shirahige, Y., Nanjoh, A., Andou, N., Ohue, H., Ishino-Arao, Y. (1988). "Cysteine biosynthesis in Saccharomyces cerevisiae: mutation that confers cystathionine beta-synthase deficiency." J Bacteriol 170:5883-5889.3056921
  • Schreve, J. L., Sin, J. K., Garrett, J. M. (1998). "The Saccharomyces cerevisiae YCC5 (YCL025c) gene encodes an amino acid permease, Agp1, which transports asparagine and glutamine." J Bacteriol 180:2556-2559.9573211
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Kumagai, Hidehiko; Tanaka, Hideyuki; Sejima, Shunsuke; Yamada, Hideaki. Elimination and replacement reactions of b-chloro-L-alanine by cysteine desulfhydrase from Aerobacter aerogenes. Agricultural and Biological Chemistry (1977), 41(10), 2071-5.
External Links:
ResourceLink
CHEBI ID17561
HMDB IDHMDB00574
Pubchem Compound ID5862
Kegg IDC00097
ChemSpider ID5653
FOODB IDFDB012678
WikipediaCysteine
BioCyc IDCYS

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur from cysteine to produce alanine. It supplies the inorganic sulfur for iron- sulfur (Fe-S) clusters. Involved in both tRNA-processing and mitochondrial metabolism
Gene Name:
NFS1
Uniprot ID:
P25374
Molecular weight:
54466.5
Reactions
L-cysteine + [enzyme]-cysteine → L-alanine + [enzyme]-S-sulfanylcysteine.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
Not Available
Uniprot ID:
P53206
Molecular weight:
42800.5
Reactions
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
Transforms O-acetylhomoserine into homocysteine and O- acetylserine into cysteine
Gene Name:
MET17
Uniprot ID:
P06106
Molecular weight:
48671.39844
Reactions
O-acetyl-L-homoserine + methanethiol → L-methionine + acetate.
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Gene Name:
CYS3
Uniprot ID:
P31373
Molecular weight:
42541.69922
Reactions
L-cystathionine + H(2)O → L-cysteine + NH(3) + 2-oxobutanoate.
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40506
Molecular weight:
41892.69922
Reactions
CTP + (R)-4'-phosphopantothenate + L-cysteine → CMP + PPi + N-((R)-4'-phosphopantothenoyl)-L-cysteine.
General function:
Involved in glutamate-cysteine ligase activity
Specific function:
ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine
Gene Name:
GSH1
Uniprot ID:
P32477
Molecular weight:
78252.89844
Reactions
ATP + L-glutamate + L-cysteine → ADP + phosphate + gamma-L-glutamyl-L-cysteine.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q12198
Molecular weight:
64222.80078
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in nucleotide binding
Specific function:
ATP + L-cysteine + tRNA(Cys) = AMP + diphosphate + L-cysteinyl-tRNA(Cys)
Gene Name:
Not Available
Uniprot ID:
P53852
Molecular weight:
87529.5
Reactions
ATP + L-cysteine + tRNA(Cys) → AMP + diphosphate + L-cysteinyl-tRNA(Cys).
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
STR2
Uniprot ID:
P47164
Molecular weight:
72349.89844
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Plays a role in the turnover of the vacuolar glutathione and in the supply of growth requirements during nitrogen starvation
Gene Name:
ECM38
Uniprot ID:
Q05902
Molecular weight:
73179.79688
Reactions
(5-L-glutamyl)-peptide + an amino acid → peptide + 5-L-glutamyl amino acid.

Transporters

General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
GAP1
Uniprot ID:
P19145
Molecular weight:
65654.89844
General function:
Involved in transport
Specific function:
High affinity transport of glutamine. Also transport Leu, Ser, Thr, Cys, Met and Asn
Gene Name:
GNP1
Uniprot ID:
P48813
Molecular weight:
73597.39844
General function:
Involved in transport
Specific function:
Required for high-affinity tryptophan transport. Also transports cysteine, phenyalanine and tyrosine
Gene Name:
TAT2
Uniprot ID:
P38967
Molecular weight:
65403.80078
General function:
Involved in transport
Specific function:
Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:
BAP2
Uniprot ID:
P38084
Molecular weight:
67669.60156
General function:
Involved in transport
Specific function:
High-affinity transport of valine and tyrosine. Low- affinity transport of tryptophan. Can also transport L-cysteine
Gene Name:
TAT1
Uniprot ID:
P38085
Molecular weight:
68756.89844
General function:
Involved in transport
Specific function:
Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:
BAP3
Uniprot ID:
P41815
Molecular weight:
67364.39844
General function:
Involved in transport
Specific function:
Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:
AGP1
Uniprot ID:
P25376
Molecular weight:
69670.70313