Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:31:18 UTC

Update Date

2021-09-26 22:55:38 UTC

HMDB ID

HMDB0246504

Secondary Accession Numbers

None

Metabolite Identification

Common Name

P-Toluenesulfonamide

Description

toluene-4-sulfonamide, also known as p-tosylamide or p-tolylsulfonamide, 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. Based on a literature review very few articles have been published on toluene-4-sulfonamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). P-toluenesulfonamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically P-Toluenesulfonamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Toluenesulfonamide	ChEBI
p-Toluenesulfonamide	ChEBI
p-Tolylsulfonamide	ChEBI
p-Tosylamide	ChEBI
Tosylamide	ChEBI
4-Toluenesulphonamide	Generator
p-Toluenesulphonamide	Generator
p-Tolylsulphonamide	Generator
Toluene-4-sulphonamide	Generator
4-Methylbenzenesulfonamide	MeSH
4-Toluenesulfonamide hydrochloride	MeSH
4-Toluenesulfonamide, 6-(14)C-labeled	MeSH
4-Toluenesulfonamide, mercury (+2) salt (1:1)	MeSH
4-Toluenesulfonamide, mercury (+2) salt (2:1)	MeSH
4-Toluenesulfonamide, monopotassium salt	MeSH
4-Toluenesulfonamide, monosilver salt	MeSH
4-Toluenesulfonamide, monosodium salt	MeSH
4-Toluenesulfonylamide	MeSH
Para-toluenesulfonamide	MeSH
Para-toluenesulphonamide	MeSH
4-Methylbenzenesulphonamide	Generator

Chemical Formula

C₇H₉NO₂S

Average Molecular Weight

171.21

Monoisotopic Molecular Weight

171.035399708

IUPAC Name

4-methylbenzene-1-sulfonamide

Traditional Name

p-toluenesulfonamide

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

InChI Key

LMYRWZFENFIFIT-UHFFFAOYSA-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
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonamide (CHEBI:34435 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

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	0.72	ALOGPS
logP	1.09	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.26 m³·mol⁻¹	ChemAxon
Polarizability	16.85 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 Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	134.939	30932474
DeepCCS	[M-H]-	131.112	30932474
DeepCCS	[M-2H]-	168.681	30932474
DeepCCS	[M+Na]+	144.22	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.1	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	134.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
P-Toluenesulfonamide	CC1=CC=C(C=C1)S(N)(=O)=O	2472.2	Standard polar	33892256
P-Toluenesulfonamide	CC1=CC=C(C=C1)S(N)(=O)=O	1644.8	Standard non polar	33892256
P-Toluenesulfonamide	CC1=CC=C(C=C1)S(N)(=O)=O	1691.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
P-Toluenesulfonamide,1TMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C1	1813.4	Semi standard non polar	33892256
P-Toluenesulfonamide,1TMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C1	1625.3	Standard non polar	33892256
P-Toluenesulfonamide,1TMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C1	2139.7	Standard polar	33892256
P-Toluenesulfonamide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1772.8	Semi standard non polar	33892256
P-Toluenesulfonamide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1844.7	Standard non polar	33892256
P-Toluenesulfonamide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2171.6	Standard polar	33892256
P-Toluenesulfonamide,1TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C1	2024.5	Semi standard non polar	33892256
P-Toluenesulfonamide,1TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C1	1881.1	Standard non polar	33892256
P-Toluenesulfonamide,1TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C1	2229.4	Standard polar	33892256
P-Toluenesulfonamide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2257.1	Semi standard non polar	33892256
P-Toluenesulfonamide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2306.8	Standard non polar	33892256
P-Toluenesulfonamide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2300.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - P-Toluenesulfonamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-782f24df64659fdb5d45	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - P-Toluenesulfonamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 30V, Negative-QTOF	splash10-00di-0900000000-ff335164570c6f54526a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 45V, Negative-QTOF	splash10-0ab9-2900000000-397efe2089aae059e14f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 75V, Negative-QTOF	splash10-056r-9400000000-96f18ebfbdd1480e2333	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 60V, Negative-QTOF	splash10-0a6r-7900000000-2194a90e925547579078	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 15V, Negative-QTOF	splash10-00di-0900000000-bc8d6e7117cdf4b25939	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 15V, Negative-QTOF	splash10-00di-0900000000-b0ccf286f173a39245b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 30V, Negative-QTOF	splash10-00di-0900000000-1453b294156dc83d9cf8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 60V, Negative-QTOF	splash10-0a6r-5900000000-9a8941a2aba77d52f786	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 45V, Negative-QTOF	splash10-05fr-1900000000-51977472240dd2e2c884	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 120V, Negative-QTOF	splash10-03di-9000000000-09c06a6ac4640101f342	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 150V, Negative-QTOF	splash10-03di-9000000000-82daff1a7de9cc6bc782	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 90V, Negative-QTOF	splash10-01t9-9100000000-1dfa1b7145ed1fe6894d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 90V, Negative-QTOF	splash10-01t9-9100000000-aeec1cc6c2d88c347cf4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 75V, Negative-QTOF	splash10-056r-9500000000-6719240579cb661a9089	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 45V, Positive-QTOF	splash10-014l-4900000000-9d7175ea486d4cad477d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 30V, Positive-QTOF	splash10-0aor-1900000000-86d5d6a3a5ec7ceba0de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 55V, Positive-QTOF	splash10-0a4i-0900000000-48e38f032bf8f1e26fba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 35V, Positive-QTOF	splash10-0aou-4900000000-b820a17eb7c07078e3bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 20V, Positive-QTOF	splash10-014i-0900000000-40b4690608d7404c5c74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 10V, Positive-QTOF	splash10-0a4i-0900000000-a1a385bbfd32cb0dacb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 35V, Positive-QTOF	splash10-0a4i-0900000000-3403dc4c9967d5f8241c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 80V, Positive-QTOF	splash10-0006-9100000000-0a1a7921a4429d14a0fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 150V, Positive-QTOF	splash10-014i-9000000000-526b29d4d56c253282b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 55V, Positive-QTOF	splash10-014l-7900000000-d3b1e7a1b5cdcd71084a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - P-Toluenesulfonamide 75V, Positive-QTOF	splash10-0006-9100000000-f8813b1334166ba0a564	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6033

KEGG Compound ID

C14412

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6269

PDB ID

Not Available

ChEBI ID

34435

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1698711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for P-Toluenesulfonamide (HMDB0246504)

MOL for HMDB0246504 (P-Toluenesulfonamide)

3D MOL for HMDB0246504 (P-Toluenesulfonamide)

3D SDF for HMDB0246504 (P-Toluenesulfonamide)

3D-SDF for HMDB0246504 (P-Toluenesulfonamide)

PDB for HMDB0246504 (P-Toluenesulfonamide)

3D PDB for HMDB0246504 (P-Toluenesulfonamide)

SMILES for HMDB0246504 (P-Toluenesulfonamide)

INCHI for HMDB0246504 (P-Toluenesulfonamide)

Structure for HMDB0246504 (P-Toluenesulfonamide)

3D Structure for HMDB0246504 (P-Toluenesulfonamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra