Record Information
Version1.0
Creation Date2016-07-13 19:44:11 UTC
Update Date2016-09-23 18:44:53 UTC
LmdbLMDB00183
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Cysteine
DescriptionCysteine is a naturally occurring, sulfur-containing amino acid that is found in most proteins, although only in small quantities. Cysteine is unique amongst the twenty natural amino acids as it contains a thiol group. Thiol groups can undergo oxidation/reduction (redox) reactions; when cysteine is oxidized it can form cystine, which is two cysteine residues joined by a disulfide bond. This reaction is reversible: as reduction of this disulphide bond regenerates two cysteine molecules. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Cysteine is often involved in electron-transfer reactions, and help the enzyme catalyze its reaction. Cysteine is also part of the antioxidant glutathione. N-acetyl-L-cysteine (NAC) is a form of cysteine where an acetyl group is attached to cysteine's nitrogen atom and is sold as a dietary supplement. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder - cystine was first isolated from kidney stones. As cysteine contains a sulphydryl group, it can undergo redox reactions. Oxidation of cysteine can produce a disulfide bond with another thiol, or further oxidation can produce sulphfinic or sulfonic acids. The cysteine thiol group is also a nucleophile and can undergo addition and substitution reactions. Thiol groups become much more reactive when they are ionized, and cysteine residues in proteins have pKa values close to neutrality, so are often in their reactive thiolate form in the cell. The thiol group also has a high affinity for heavy metals and proteins containing cysteine will bind metals such as mercury, lead and cadmium tightly. Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is an important source of sulfur in animal 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. (http://en.wikipedia.org/wiki/Cysteine). Cysteine is important in energy metabolism. As cystine, it is a structural component of many tissues and hormones. Cysteine has clinical uses ranging from baldness to psoriasis to preventing smoker's hack. In some cases, oral cysteine therapy has proved excellent for treatment of asthmatics, enabling them to stop theophylline and other medications. Cysteine also enhances the effect of topically applied silver, tin and zinc salts in preventing dental cavities. In the future, cysteine may play a role in the treatment of cobalt toxicity, diabetes, psychosis, cancer and seizures. (http://www.dcnutrition.com/AminoAcids/).
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Amino-3-mercaptopropanoic acidChEBI
(2R)-2-Amino-3-sulfanylpropanoic acidChEBI
(R)-2-Amino-3-mercaptopropanoic acidChEBI
CChEBI
CysChEBI
CYSTEINEChEBI
e 920ChEBI
e-920ChEBI
e920ChEBI
FREE cysteineChEBI
L-2-Amino-3-mercaptopropionic acidChEBI
L-CysteinChEBI
L-ZysteinChEBI
EcolanKegg
(2R)-2-Amino-3-mercaptopropanoateGenerator
(2R)-2-Amino-3-sulfanylpropanoateGenerator
(2R)-2-Amino-3-sulphanylpropanoateGenerator
(2R)-2-Amino-3-sulphanylpropanoic acidGenerator
(R)-2-Amino-3-mercaptopropanoateGenerator
L-2-Amino-3-mercaptopropionateGenerator
(+)-2-Amino-3-mercaptopropionic acidHMDB
(R)-(+)-CysteineHMDB
(R)-2-Amino-3-mercapto-propanoateHMDB
(R)-2-Amino-3-mercapto-propanoic acidHMDB
(R)-CysteineHMDB
2-Amino-3-mercaptopropanoateHMDB
2-Amino-3-mercaptopropanoic acidHMDB
2-Amino-3-mercaptopropionateHMDB
2-Amino-3-mercaptopropionic acidHMDB
3-Mercapto-L-alanineHMDB
AcetylcysteineHMDB
alpha-Amino-beta-thiolpropionic acidHMDB
b-MercaptoalanineHMDB
beta-MercaptoalanineHMDB
CarbocysteineHMDB
CisteinaHMDB
CisteinumHMDB
CysteinHMDB
CysteinumHMDB
Half-cystineHMDB
L CysteineHMDB
L-(+)-CysteineHMDB
L-2-Amino-3-mercaptopropanoateHMDB
L-2-Amino-3-mercaptopropanoic acidHMDB
PolycysteineHMDB
ThioserineHMDB
Cysteine hydrochlorideHMDB
Zinc cysteinateHMDB
Half cystineHMDB
Chemical FormulaC3H7NO2S
Average Molecular Weight121.158
Monoisotopic Molecular Weight121.019749163
IUPAC Name(2R)-2-amino-3-sulfanylpropanoic acid
Traditional NameL-cysteine
CAS Registry Number52-90-4
SMILES
N[C@@H](CS)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyXUJNEKJLAYXESH-REOHCLBHSA-N
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0950000000-df7e91c95b610ff21c79Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0940000000-aefe34765fb447090a23Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0970000000-10a155c40ea499023052Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0940000000-037a3a34651c3154b3b3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-118c43e33861a6baa8d2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-0690100000-0aeb88fd507505e6b718Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0950000000-df7e91c95b610ff21c79Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0940000000-aefe34765fb447090a23Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0970000000-10a155c40ea499023052Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0940000000-037a3a34651c3154b3b3Spectrum
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0uk9-5619100000-8cb2558373966174ced3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9850000000-118c43e33861a6baa8d2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gi0-0960000000-03b2097de6f9637d29cbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9100000000-4553906a941a5e87ec97Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-9200000000-cfaf705cd0452d428454Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9600000000-374c5872d68662832769Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-ddbd3df6b8dbb280ffbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-320a2c77443b80ebf733Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0089-0900000000-9dcd3d757c5cd11eb18eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-212e081fe83ad70de0adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-2eb01f41c225f614db24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-a19834eb7cb9f211fdf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2458f2587761e779ed93Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-77e590f0ed26f69b31c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-7b1857997392b006b95fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-3900000000-bc268c27ed5706a4bbd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-00di-0900000000-4573390bccc238e3c91bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-212e081fe83ad70de0adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-7b1857997392b006b95fSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-001i-9000000000-5dc69d3b59bd15290aefSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9100000000-ed3c9c47ed98679090abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-00di-2900000000-8bb219d17ccdf7ac0a5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-e623d5a27b5075c82b4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-056r-9100000000-4e26cc13af7c878115f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-9600000000-4352a7b437c34c04d9f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-7b4cd034c717561c61ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f351cbca6ffed356a9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6900000000-51ba0df80cc33423420bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-4aa2b707c391d5838d29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-95c7672c7836c0fc51c9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Kidney
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified11.803 uMNot AvailablePorcine details
SerumDetected and Quantified9.409 uMNot AvailablePorcine details
SerumDetected and Quantified3.797 uMNot AvailablePorcine details
SerumDetected and Quantified11.308 uMNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDDB00151
HMDB IDHMDB0000574
FooDB IDFDB012678
Phenol Explorer IDNot Available
KNApSAcK IDC00001351
BiGG ID33843
BioCyc IDCYS
METLIN ID5556
PDB IDNot Available
Wikipedia LinkCysteine
Chemspider ID5653
ChEBI ID17561
PubChem Compound ID5862
Kegg Compound IDC00097
YMDB IDYMDB00046
ECMDB IDECMDB00574
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available