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
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
Physico-Chemical Properties - Experimental
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
Predicted GC-MSL-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cysteine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cysteine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cysteine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9600000000-374c5872d686628327692012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-ddbd3df6b8dbb280ffba2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-320a2c77443b80ebf7332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0089-0900000000-9dcd3d757c5cd11eb18e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-212e081fe83ad70de0ad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-2eb01f41c225f614db242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-a19834eb7cb9f211fdf22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2458f2587761e779ed932012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-77e590f0ed26f69b31c02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-7b1857997392b006b95f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-3900000000-bc268c27ed5706a4bbd22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-00di-0900000000-4573390bccc238e3c91b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-212e081fe83ad70de0ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-7b1857997392b006b95f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-001i-9000000000-5dc69d3b59bd15290aef2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9100000000-ed3c9c47ed98679090ab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-00di-2900000000-8bb219d17ccdf7ac0a5d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-e623d5a27b5075c82b4d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-056r-9100000000-4e26cc13af7c878115f72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-9600000000-4352a7b437c34c04d9f02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-7b4cd034c717561c61dd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f351cbca6ffed356a9b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6900000000-51ba0df80cc33423420b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-4aa2b707c391d5838d292016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-95c7672c7836c0fc51c92016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.