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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:56:48 UTC

Update Date

2022-09-22 18:34:53 UTC

HMDB ID

HMDB0341401

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tosyl-L-lysyl-chloromethane

Description

N-[(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

MOL SDF PDB SMILES InChI

TCK
  Mrv0541 02241214122D          

 22 22  0  0  0  0            999 V2000
   -0.9577    0.8730    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577    1.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577    0.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827    0.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    0.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0202    0.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4327    0.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0202    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2577    0.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327    0.8730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798    0.1586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1327   -0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577   -0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    0.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173   -0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3423   -0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5798   -1.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042    0.1586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -1.9848    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  3  1  2  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
 12 11  1  1  0  0  0
 11  1  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 12 21  1  6  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341401

> <DATABASE_NAME>
hmdb

> <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_KEY>
RDFCSSHDJSZMTQ-ZDUSSCGKSA-N

> <FORMULA>
C14H21ClN2O3S

> <MOLECULAR_WEIGHT>
332.846

> <EXACT_MASS>
332.096140945

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.05600858506551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
1.6842149412195286

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.47033956261632

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.396283372043124

> <JCHEM_PKA_STRONGEST_BASIC>
9.778802862557322

> <JCHEM_POLAR_SURFACE_AREA>
89.26

> <JCHEM_REFRACTIVITY>
84.3488

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
C14H21clN2O3S

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: TCK                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0      -1.788   1.630   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      -1.788   3.170   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -1.788   0.090   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.328   1.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.098   0.296   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.638   0.296   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.408   1.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.638   2.963   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.098   2.963   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.948   1.630   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.248   1.630   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.522   0.296   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.248  -1.038   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.788  -1.038   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.062   0.296   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.832  -1.038   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.372  -1.038   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.142  -2.371   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.682  -2.371   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.522  -2.371   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -0.568   0.296   0.000  0.00  0.00           H+0
HETATM   22 Cl   UNK     0      -0.248  -3.705   0.000  0.00  0.00          Cl+0
CONECT    1    2    4    3   11                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    7                                                            
CONECT   11   12    1                                                       
CONECT   12   11   13   15   21                                             
CONECT   13   12   14   20                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   13   22                                                       
CONECT   21   12                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[(1S)-5-Amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulphonamide	Generator
Tosyl-L-lysine chloromethyl ketone	ChEMBL
Chloromethyl ketone, tosyllysine	MeSH
TLCK	MeSH
Chloromethane, tosyllysyl	MeSH
Chlorotosylamidoaminoheptanone	MeSH
Ketone, tosyllysine chloromethyl	MeSH
Tosyllysine chloromethyl ketone	MeSH
Tosyllysyl chloromethane	MeSH

Chemical Formula

C₁₄H₂₁ClN₂O₃S

Average Molecular Weight

332.846

Monoisotopic Molecular Weight

332.096140945

IUPAC Name

(3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido

Traditional Name

C14H21clN2O3S

CAS Registry Number

Not 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 Key

RDFCSSHDJSZMTQ-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

P-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonic acid derivative (CHEBI:9640 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.82	ALOGPS
logP	1.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.4	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.26 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	84.35 m³·mol⁻¹	ChemAxon
Polarizability	34.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tosyl-L-lysyl-chloromethane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6190000000-bf4c801ce4acc245d549	2017-08-28	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 10V, Positive-QTOF	splash10-02u0-0629000000-a16d089ab5b29d8c3699	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 20V, Positive-QTOF	splash10-03dj-1912000000-e12eca1dc184d23cd377	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 40V, Positive-QTOF	splash10-0fau-9200000000-e9178c04729f2fe9002f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 10V, Negative-QTOF	splash10-001i-0219000000-3f8db1029f7b0ef57a31	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 20V, Negative-QTOF	splash10-0a5a-2974000000-d666a600fe86b38f1c41	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tosyl-L-lysyl-chloromethane 40V, Negative-QTOF	splash10-0a4i-4900000000-5a0017a1524af05051d1	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08603

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00896

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73094

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Tosyl-L-lysyl-chloromethane (HMDB0341401)

MOL for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

3D MOL for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

3D SDF for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

3D-SDF for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

PDB for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

3D PDB for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

SMILES for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

INCHI for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

Structure for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

3D Structure for HMDB0341401 (Tosyl-L-lysyl-chloromethane)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra