Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2020-09-17 15:38:37 UTC
Primary IDFDB012678
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
Synonyms
SynonymSource
(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
(2R)-2-amino-3-SulphanylpropanoateGenerator
(2R)-2-amino-3-Sulphanylpropanoic acidGenerator
(R)-2-Amino-3-mercaptopropionic acidbiospider
α-amino-β-Thiolpropionic acidbiospider
β-Mercaptoalaninebiospider
2-Amino-3-mercapto-, (R)-biospider
2-Amino-3-mercaptopropanoic acid, (R)-biospider
3-Mercapto-L-Alaninebiospider
alpha-Amino-beta-mercaptopropanoic acid, L-biospider
alpha-Amino-beta-mercaptopropionic acid, L-biospider
alpha-Amino-beta-thiolpropionic acid, L-biospider
beta-Mercaptoalanine, L-biospider
CYSbiospider
Cysteinebiospider
Cysteine, INN; L-formdb_source
Ecolan (TN)biospider
L-2-amino-3-MercaptopropionateGenerator
L-Alanine, 3-mercapto-biospider
L-CYSbiospider
L-Cysteinebiospider
Propanoic Acid, 2-amino-3-mercapto-, (R)-biospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 29.74%; H 5.82%; N 11.56%; O 26.41%; S 26.47%DFC
Melting PointMp 178° dec.DFC
Boiling PointNot Available
Experimental Water Solubility277 mg/mL at 25 oCBEILSTEIN
Experimental logP-2.49HANSCH,C ET AL. (1995)
Experimental pKapKa3 10.46 (SH)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +26.5 (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Cysteine, 4 TMS, GC-MS Spectrumsplash10-00kb-0950000000-df7e91c95b610ff21c79Spectrum
GC-MSL-Cysteine, 4 TMS, GC-MS Spectrumsplash10-00kb-0940000000-aefe34765fb447090a23Spectrum
GC-MSL-Cysteine, 4 TMS, GC-MS Spectrumsplash10-00kb-0970000000-10a155c40ea499023052Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00kb-0940000000-037a3a34651c3154b3b3Spectrum
GC-MSL-Cysteine, 4 TMS, GC-MS Spectrumsplash10-00di-9850000000-118c43e33861a6baa8d2Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-014j-0690100000-0aeb88fd507505e6b718Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00kb-0950000000-df7e91c95b610ff21c79Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00kb-0940000000-aefe34765fb447090a23Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00kb-0970000000-10a155c40ea499023052Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00kb-0940000000-037a3a34651c3154b3b3Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-0uk9-5619100000-8cb2558373966174ced3Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-00di-9850000000-118c43e33861a6baa8d2Spectrum
GC-MSL-Cysteine, non-derivatized, GC-MS Spectrumsplash10-0gi0-0960000000-03b2097de6f9637d29cbSpectrum
Predicted GC-MSL-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-9100000000-4553906a941a5e87ec97Spectrum
Predicted GC-MSL-Cysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9200000000-cfaf705cd0452d428454Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9600000000-374c5872d68662832769Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-ddbd3df6b8dbb280ffbaSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-320a2c77443b80ebf733Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0089-0900000000-9dcd3d757c5cd11eb18eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-212e081fe83ad70de0adSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-2eb01f41c225f614db24Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-a19834eb7cb9f211fdf2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2458f2587761e779ed93Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-77e590f0ed26f69b31c0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-7b1857997392b006b95fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-3900000000-bc268c27ed5706a4bbd2Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-00di-0900000000-4573390bccc238e3c91bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-212e081fe83ad70de0adSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-7b1857997392b006b95fSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-001i-9000000000-5dc69d3b59bd15290aefSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-9600000000-4352a7b437c34c04d9f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-7b4cd034c717561c61ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f351cbca6ffed356a9bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6900000000-51ba0df80cc33423420bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-4aa2b707c391d5838d29Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-95c7672c7836c0fc51c9Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5653
ChEMBL IDCHEMBL863
KEGG Compound IDC00097
Pubchem Compound ID5862
Pubchem Substance IDNot Available
ChEBI ID17561
Phenol-Explorer IDNot Available
DrugBank IDDB00151
HMDB IDHMDB00574
CRC / DFC (Dictionary of Food Compounds) IDHJQ86-N:HJQ81-I
EAFUS ID813
Dr. Duke IDCYSTEINE
BIGG ID33843
KNApSAcK IDC00001351
HET IDCYS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1018061
SuperScent IDNot Available
Wikipedia IDL-Cysteine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti AddisonianDUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cytotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti ophthalmicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
glutathionergicDUKE
ophthalmic antialkaliDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
Enzymes
NameGene NameUniProt ID
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Glutathione synthetaseGSSP48637
Molybdenum cofactor sulfuraseMOCOSQ96EN8
Glutamate--cysteine ligase catalytic subunitGCLCP48506
Cystathionine gamma-lyaseCTHP32929
Cysteine sulfinic acid decarboxylaseCSADQ9Y600
Gamma-glutamylcyclotransferaseGGCTO75223
Phosphopantothenate--cysteine ligasePPCSQ9HAB8
Glutamate--cysteine ligase regulatory subunitGCLMP48507
Thiamine transporter 2SLC19A3Q9BZV2
Cysteine--tRNA ligase, cytoplasmicCARSP49589
Cysteine dioxygenaseCDO-1Q16857
Pathways
NameSMPDB LinkKEGG Link
Cysteine MetabolismSMP00013 map00270
Glutathione MetabolismSMP00015 map00480
Glycine and Serine MetabolismSMP00004 map00260
Methionine MetabolismSMP00033 map00270
Pantothenate and CoA BiosynthesisSMP00027 map00770
Taurine and Hypotaurine MetabolismSMP00021 map00430
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sulfury
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.