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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:08:04 UTC
Update Date2021-09-14 15:00:49 UTC
HMDB IDHMDB0034323
Secondary Accession Numbers
  • HMDB34323
Metabolite Identification
Common 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. Allyl cysteine is currently being investigated as a potential cholesterol lowering agent and as a chemopreventive. S-Allylcysteine is a very strong basic compound (based on its pKa). S-Allylcysteine is a cooked and roasted tasting compound. Outside of the human body, 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. It is a derivative of the amino acid cysteine in which an allyl group has been added to the sulfur atom. S-Allyl cysteine (SAC) is an organic compound that is a natural constituent of fresh garlic.
Structure
Data?1563862545
Synonyms
ValueSource
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
Chemical FormulaC6H11NO2S
Average Molecular Weight161.222
Monoisotopic Molecular Weight161.051049291
IUPAC Name2-amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid
Traditional NameS-allyl cysteine
CAS Registry Number21593-77-1
SMILES
NC(CSCC=C)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available134.13431661259
DarkChem[M-H]-PredictedNot Available129.03431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
S-Allylcysteine,1TMS,#11433.2728https://arxiv.org/abs/1905.12712
S-Allylcysteine,1TMS,#21501.8597https://arxiv.org/abs/1905.12712
S-Allylcysteine,1TBDMS,#11654.8837https://arxiv.org/abs/1905.12712
S-Allylcysteine,1TBDMS,#21717.1893https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6472ab7f2d2b13b420922017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0007-9500000000-6130c45418f29c7eb2ab2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-5900000000-8c89fd146060416fb06f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9300000000-9edb4d3a5be841c6a27e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-8dde9c26474a4aa9cf9c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-4900000000-5ea2674e8ab9863410c82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9500000000-584904bc5c18c5d83a032017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-9100000000-847061c3a2deccc782b72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-f82699e969ddcd674ff22021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-9100000000-9c1e17063ccb59bc374a2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bfbf6eb00eab590319dc2021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012675
KNApSAcK IDNot Available
Chemspider ID88744
KEGG Compound IDC16759
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkS-Allyl cysteine
METLIN IDNot Available
PubChem Compound98280
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .