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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:56:48 UTC
Update Date2022-09-22 18:34:53 UTC
HMDB IDHMDB0341401
Secondary Accession NumbersNone
Metabolite Identification
Common NameTosyl-L-lysyl-chloromethane
DescriptionN-[(1S)-5-amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulfonamide belongs to the class of organic compounds known as p-toluenesulfonamides. These are aromatic heterocyclic compounds containing a toluene that is p-substituted with a sulfonamide group. N-[(1S)-5-amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulfonamide is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
N-[(1S)-5-Amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulphonamideGenerator
Tosyl-L-lysine chloromethyl ketoneChEMBL
Chloromethyl ketone, tosyllysineMeSH
TLCKMeSH
Chloromethane, tosyllysylMeSH
ChlorotosylamidoaminoheptanoneMeSH
Ketone, tosyllysine chloromethylMeSH
Tosyllysine chloromethyl ketoneMeSH
Tosyllysyl chloromethaneMeSH
Chemical FormulaC14H21ClN2O3S
Average Molecular Weight332.846
Monoisotopic Molecular Weight332.096140945
IUPAC Name(3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido
Traditional NameC14H21clN2O3S
CAS Registry NumberNot Available
SMILES
[H][C@@](CCCCN)(NS(=O)(=O)C1=CC=C(C)C=C1)C(=O)CCl
InChI Identifier
InChI=1S/C14H21ClN2O3S/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16/h5-8,13,17H,2-4,9-10,16H2,1H3/t13-/m0/s1
InChI KeyRDFCSSHDJSZMTQ-ZDUSSCGKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-toluenesulfonamides. These are aromatic heterocyclic compounds containing a toluene that is p-substituted with a sulfonamide group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentP-toluenesulfonamides
Alternative Parents
Substituents
  • P-toluenesulfonamide
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Organosulfonic acid amide
  • Alpha-haloketone
  • Alpha-chloroketone
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Ketone
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.82ALOGPS
logP1.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.4ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.26 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.35 m³·mol⁻¹ChemAxon
Polarizability34.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tosyl-L-lysyl-chloromethane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6190000000-bf4c801ce4acc245d5492017-08-28Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 10V, Positive-QTOFsplash10-02u0-0629000000-a16d089ab5b29d8c36992017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 20V, Positive-QTOFsplash10-03dj-1912000000-e12eca1dc184d23cd3772017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 40V, Positive-QTOFsplash10-0fau-9200000000-e9178c04729f2fe9002f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 10V, Negative-QTOFsplash10-001i-0219000000-3f8db1029f7b0ef57a312017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 20V, Negative-QTOFsplash10-0a5a-2974000000-d666a600fe86b38f1c412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 40V, Negative-QTOFsplash10-0a4i-4900000000-5a0017a1524af05051d12017-07-26Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08603
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00896
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73094
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]