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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 20:29:18 UTC
Update Date2017-10-23 19:04:03 UTC
HMDB IDHMDB0003417
Secondary Accession Numbers
  • HMDB03417
Metabolite Identification
Common NameD-Cysteine
DescriptionD-Cysteine is a naturally occurring enantiomer of L-Cysteine. It is a non-proteogenic sulfur-containing amino acid. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder − cystine was first isolated from kidney stones. (wikipedia) D-cysteine can be generated from L-cysteine via cysteine racemase. D-Cysteine is known to be toxic to bacteria and several bacteria (and plants) have developed and enzyme called D-cysteine desulfhydrase (EC 4.1.99.4). This enzyme decomposes D-cysteine into pyruvate, H2S, and NH3. (PMID: 15720402 ).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-amino-3-Mercaptopropanoic acidChEBI
(2S)-2-amino-3-Sulfanylpropanoic acidChEBI
(S)-2-amino-3-Mercaptopropanoic acidChEBI
D-amino-3-Mercaptopropionic acidChEBI
D-CysteinChEBI
D-ZysteinChEBI
DCYChEBI
(2S)-2-amino-3-MercaptopropanoateGenerator
(2S)-2-amino-3-SulfanylpropanoateGenerator
(2S)-2-amino-3-SulphanylpropanoateGenerator
(2S)-2-amino-3-Sulphanylpropanoic acidGenerator
(S)-2-amino-3-MercaptopropanoateGenerator
D-amino-3-MercaptopropionateGenerator
Chemical FormulaC3H7NO2S
Average Molecular Weight121.15
Monoisotopic Molecular Weight121.019749643
IUPAC Name(2S)-2-amino-3-sulfanylpropanoic acid
Traditional NameL cysteine
CAS Registry Number921-01-7
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-/m1/s1
InChI KeyXUJNEKJLAYXESH-UWTATZPHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cysteine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • D-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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability11.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9100000000-4553906a941a5e87ec97View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-9200000000-cfaf705cd0452d428454View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-056r-9300000000-ed3d829a54e4ac06325dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-224425097c9b1883d266View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-9000000000-39cb21d5fd8f893ba8fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-9600000000-4352a7b437c34c04d9f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-7b4cd034c717561c61ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f351cbca6ffed356a9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6900000000-51ba0df80cc33423420bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-4aa2b707c391d5838d29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-95c7672c7836c0fc51c9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified8.643 +/- 2.11 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023168
KNApSAcK IDNot Available
Chemspider ID83819
KEGG Compound IDC00793
BioCyc IDD-CYSTEINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92851
PDB IDDCY
ChEBI ID16375
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tsukamoto S, Kanegae T, Nagoya T, Shimamura M, Mieda Y, Nomura M, Hojo K, Okubo H: Effects of amino acids on acute alcohol intoxication in mice--concentrations of ethanol, acetaldehyde, acetate and acetone in blood and tissues. Arukoru Kenkyuto Yakubutsu Ison. 1990 Oct;25(5):429-40. [PubMed:2275637 ]
  2. Riemenschneider A, Wegele R, Schmidt A, Papenbrock J: Isolation and characterization of a D-cysteine desulfhydrase protein from Arabidopsis thaliana. FEBS J. 2005 Mar;272(5):1291-304. [PubMed:15720402 ]