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Showing Compound S-Allylcysteine (FDB012675)

Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2019-11-26 03:07:21 UTC
Primary IDFDB012675
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-Allylcysteine
DescriptionS-Allylcysteine, also known as L-deoxyalliin, 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. S-Allylcysteine is a very strong basic compound (based on its pKa). S-Allylcysteine is a cooked and roasted tasting compound. S-Allylcysteine is found, on average, in the highest concentration within soft-necked garlics. S-Allylcysteine has also been detected, but not quantified in, garden onions and onion-family vegetables. This could make S-allylcysteine a potential biomarker for the consumption of these foods.
CAS Number21593-77-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
L-DeoxyallIInHMDB
S-2-Propenyl-L-cysteineHMDB
S-Allyl-L -cysteineHMDB
Allyl cysteineHMDB
2-Amino-3-(prop-2-en-1-ylsulfanyl)propanoateGenerator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoateGenerator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoic acidGenerator
S-AllylcysteineMeSH
L-Cysteine, S-2-propenyl-biospider
L-deoxyallIInbiospider
S-allyl-l -cysteinebiospider
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
Polarizability16.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H11NO2S
IUPAC name2-amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid
InChI IdentifierInChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
InChI KeyZFAHNWWNDFHPOH-UHFFFAOYSA-N
Isomeric SMILESNC(CSCC=C)C(O)=O
Average Molecular Weight161.222
Monoisotopic Molecular Weight161.051049291
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
  • 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
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods

Fruits and vegetables:

Herbs and spices:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 44.70%; H 6.88%; N 8.69%; O 19.85%; S 19.89%DFC
Melting PointMp 218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -16.4 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6472ab7f2d2b13b42092JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0007-9500000000-6130c45418f29c7eb2abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-5900000000-8c89fd146060416fb06fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9300000000-9edb4d3a5be841c6a27eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-8dde9c26474a4aa9cf9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-4900000000-5ea2674e8ab9863410c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9500000000-584904bc5c18c5d83a03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-9100000000-847061c3a2deccc782b7JSpectraViewer
ChemSpider ID88744
ChEMBL IDNot Available
KEGG Compound IDC16759
Pubchem Compound ID98280
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34323
CRC / DFC (Dictionary of Food Compounds) IDHJQ86-N:HJQ74-I
EAFUS ID103
Dr. Duke IDS-ALLYL-L-CYSTEINE|S-ALLYL-CYSTEINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1593931
SuperScent IDNot Available
Wikipedia IDNot Available
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 aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherogenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cholesterogenicDUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti neuroblastomicDUKE
anti NF-kappa-B35222 A substance that diminishes the rate of a chemical reaction.DUKE
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
anti proliferantDUKE
anti radicularDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
glutathione-sparingDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
mucokineticDUKE
squalene-monooxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
cooked
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).