Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2018-01-23 19:24:34 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 very strong basic compound (based on its pKa). L-Cysteine exists in all living species, ranging from bacteria to humans. L-Cysteine is a sulfury tasting compound. 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 and dates. L-Cysteine has also been detected, but not quantified in, several different foods, such as cherimoya, atlantic herrings, hyssops, lindens, and malabar spinachs. This could make L-cysteine a potential biomarker for the consumption of these foods. L-Cysteine is a potentially toxic compound.
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, MeSH
L CysteineHMDB, MeSH
L-(+)-CysteineHMDB
L-2-amino-3-MercaptopropanoateHMDB
L-2-amino-3-Mercaptopropanoic acidHMDB
PolycysteineHMDB
ThioserineHMDB
Cysteine hydrochlorideMeSH, HMDB
Zinc cysteinateMeSH, HMDB
Half cystineMeSH, HMDB
S-Butylcysteine sulphoxideGenerator
Benzamidoacetic acidChEBI
BenzamidoessigsaeureChEBI
Benzoylaminoacetic acidChEBI
BenzoylaminoessigsaeureChEBI
HippurateChEBI
HippursaeureChEBI
Phenylcarbonylaminoacetic acidChEBI
N-BenzoylglycineKEGG
BenzamidoacetateGenerator
BenzoylaminoacetateGenerator
PhenylcarbonylaminoacetateGenerator
HippateGenerator
Hippic acidGenerator
(Benzoylamino)-acetateHMDB
(Benzoylamino)-acetic acidHMDB
2-BenzamidoacetateHMDB
2-Benzamidoacetic acidHMDB
BenzoylglycineHMDB
N-BenzoylglycinateHMDB
2-Amino-4-mercaptobutyric acidChEBI
HcyChEBI
2-Amino-4-mercaptobutyrateGenerator
(2S)-2-Amino-5-(carbamimidamido)pentanoic acidChEBI
(2S)-2-Amino-5-guanidinopentanoic acidChEBI
(S)-2-Amino-5-guanidinopentanoic acidChEBI
(S)-2-Amino-5-guanidinovaleric acidChEBI
ArgChEBI
ArginineChEBI
L-(+)-ArginineChEBI
L-ArgChEBI
L-ArgininChEBI
RChEBI
(2S)-2-Amino-5-(carbamimidamido)pentanoateGenerator
(2S)-2-Amino-5-guanidinopentanoateGenerator
(S)-2-Amino-5-guanidinopentanoateGenerator
(S)-2-Amino-5-guanidinovalerateGenerator
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoateHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acidHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoateHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acidHMDB
2-Amino-5-guanidinovalerateHMDB
2-Amino-5-guanidinovaleric acidHMDB
5-[(Aminoiminomethyl)amino]-L-norvalineHMDB
L-a-Amino-D-guanidinovalerateHMDB
L-a-Amino-D-guanidinovaleric acidHMDB
L-alpha-Amino-delta-guanidinovalerateHMDB
L-alpha-Amino-delta-guanidinovaleric acidHMDB
N5-(Aminoiminomethyl)-L-ornithineHMDB
DL-Arginine acetate, monohydrateHMDB
L-Isomer arginineHMDB
Monohydrate DL-arginine acetateHMDB
L ArginineHMDB
Arginine, L isomerHMDB
Arginine, L-isomerHMDB
Hydrochloride, arginineHMDB
Arginine hydrochlorideHMDB
DL Arginine acetate, monohydrateHMDB
(1R)-1-Carboxy-2-sulphanylethan-1-aminideGenerator
3-[(2S)-2-(Naphthalene-2-sulphonamido)-3-oxo-3-(piperazin-1-yl)propyl]benzene-1-carboximidamideGenerator
(+)-2-Amino-3-mercaptopropionic acidbiospider
(2R)-2-amino-3-SulphanylpropanoateGenerator
(2R)-2-amino-3-Sulphanylpropanoic acidGenerator
(R)-2-Amino-3-mercapto-propanoatebiospider
(R)-2-Amino-3-mercapto-propanoic acidbiospider
(R)-2-Amino-3-mercaptopropionic acidbiospider
α-amino-β-Thiolpropionic acidbiospider
β-Mercaptoalaninebiospider
2-Amino-3-mercapto-, (R)-biospider
2-Amino-3-mercaptopropanoatebiospider
2-Amino-3-mercaptopropanoic acidbiospider
2-Amino-3-mercaptopropanoic acid, (R)-biospider
2-Amino-3-mercaptopropionatebiospider
2-Amino-3-mercaptopropionic acidbiospider
3-Mercapto-L-Alaninebiospider
alpha-Amino-beta-mercaptopropanoic acid, L-biospider
alpha-Amino-beta-mercaptopropionic acid, L-biospider
alpha-Amino-beta-thiolpropionic acidbiospider
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-mercaptopropanoatebiospider
L-2-Amino-3-mercaptopropanoic acidbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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-df7e91c95b610ff21c79JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0940000000-aefe34765fb447090a23JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00kb-0970000000-10a155c40ea499023052JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0940000000-037a3a34651c3154b3b3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9850000000-118c43e33861a6baa8d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-0690100000-0aeb88fd507505e6b718JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0950000000-df7e91c95b610ff21c79JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0940000000-aefe34765fb447090a23JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0970000000-10a155c40ea499023052JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0940000000-037a3a34651c3154b3b3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0uk9-5619100000-8cb2558373966174ced3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9850000000-118c43e33861a6baa8d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gi0-0960000000-03b2097de6f9637d29cbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9100000000-4553906a941a5e87ec97JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-9200000000-cfaf705cd0452d428454JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9600000000-374c5872d68662832769JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-ddbd3df6b8dbb280ffbaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-320a2c77443b80ebf733JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0089-0900000000-9dcd3d757c5cd11eb18eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-212e081fe83ad70de0adJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-2eb01f41c225f614db24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-a19834eb7cb9f211fdf2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2458f2587761e779ed93JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-77e590f0ed26f69b31c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-7b1857997392b006b95fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-3900000000-bc268c27ed5706a4bbd2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-00di-0900000000-4573390bccc238e3c91bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-212e081fe83ad70de0adJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-7b1857997392b006b95fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-9600000000-4352a7b437c34c04d9f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-7b4cd034c717561c61ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f351cbca6ffed356a9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6900000000-51ba0df80cc33423420bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-4aa2b707c391d5838d29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-95c7672c7836c0fc51c9JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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).