S-ALLYL-L-CYSTEINE (CHEM004650)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:53:17 UTC
Update Date2016-11-09 01:09:24 UTC
Accession NumberCHEM004650
Identification
Common NameS-ALLYL-L-CYSTEINE
ClassSmall Molecule
DescriptionAn S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occurs in garlic and has been found to exhibit antineoplastic activity.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
L-DeoxyalliinChEBI
S-2-Propenyl-L-cysteineChEBI
S-Allyl-L-cysteineChEBI
Allyl cysteineMeSH
(2R)-2-amino-3-Prop-2-enylsulfanylpropanoateGenerator
(2R)-2-amino-3-Prop-2-enylsulphanylpropanoateGenerator
(2R)-2-amino-3-Prop-2-enylsulphanylpropanoic acidGenerator
S-AllylcysteineMeSH
Chemical FormulaC6H11NO2S
Average Molecular Mass161.220 g/mol
Monoisotopic Mass161.051 g/mol
CAS Registry Number21593-77-1
IUPAC Name(2R)-2-amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid
Traditional NameS-allyl cysteine
SMILES[H][C@](N)(CSCC=C)C(O)=O
InChI IdentifierInChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
InChI KeyZFAHNWWNDFHPOH-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Allyl sulfur compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Carbonyl group
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.7 g/LALOGPS
logP-1.8ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.09 m³·mol⁻¹ChemAxon
Polarizability16.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029f-6900000000-b0930f7a2cca218e4ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9300000000-b192e480315b7fd0a6fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-dd1b3cdae7c67daa4b86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-5900000000-486ef994658b618b2e60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-2ef15c37acd22532bf86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-9100000000-0462b95daabc9969f1ccSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00037771
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkS-Allyl_cysteine
Chemspider IDNot Available
ChEBI ID74077
PubChem Compound ID9793905
Kegg Compound IDC16759
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21166677
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21560330
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22052207
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22981633