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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:19:33 UTC
Update Date2019-07-23 07:13:24 UTC
HMDB IDHMDB0060011
Secondary Accession Numbers
  • HMDB60011
Metabolite Identification
Common NameN-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine
DescriptionN-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine is an extremely weak basic (essentially neutral) compound (based on its pKa). These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Structure
Data?1563866004
Synonyms
ValueSource
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulfanyl}propanoateGenerator
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulphanyl}propanoateGenerator
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulphanyl}propanoic acidGenerator
Ac-atc-cysMeSH
N-Acetyl-S-(N-allylthiocarbamoyl)-L-cysteineMeSH
N-Acetyl-S-(N-allylthiocarbamoyl)cysteineMeSH
Chemical FormulaC9H14N2O3S2
Average Molecular Weight262.349
Monoisotopic Molecular Weight262.044583704
IUPAC Name2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid
Traditional Name2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NC(CSC(=S)NCC=C)C(O)=O
InChI Identifier
InChI=1S/C9H14N2O3S2/c1-3-4-10-9(15)16-5-7(8(13)14)11-6(2)12/h3,7H,1,4-5H2,2H3,(H,10,15)(H,11,12)(H,13,14)
InChI KeyDJFUZUUKZXAXBZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cysteine or derivatives
  • Acetamide
  • Dithiocarbamic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP0.54ALOGPS
logP0.64ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67.86 m³·mol⁻¹ChemAxon
Polarizability26.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9320000000-bf0cb6451be37c388a3aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9211000000-ee1133670216bdd1ba7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1930000000-f0d2b8ac546b4aefd5f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-7950000000-c742c3f56c18ed0f7dcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-095c894b0184ae1d3b27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-4290000000-ef94e8d3017f0a64553dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5a-9620000000-01bfc8a015c9f3d46008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-cfbc613da08d452851edSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5744015
PDB IDNot Available
ChEBI ID89611
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jiao D, Ho CT, Foiles P, Chung FL: Identification and quantification of the N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prev. 1994 Sep;3(6):487-92. [PubMed:8000299 ]