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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-10-01 18:02:46 UTC

Update Date

2021-10-01 18:02:46 UTC

HMDB ID

HMDB0304940

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Aminobenzenesulfonic acid

Description

2-aminobenzenesulfonic acid, also known as aniline-O-sulfonic acid or orthanilic acid, belongs to the class of organic compounds known as benzenesulfonic acids and derivatives. These are organic compounds containing a sulfonic acid or a derivative thereof that is linked to a benzene ring. 2-aminobenzenesulfonic acid is a moderately basic compound (based on its pKa).

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Aminobenzene-2-sulfonic acid	ChEBI
2-Sulfanilic acid	ChEBI
Aniline-O-sulfonic acid	ChEBI
Aniline-O-sulphonic acid	ChEBI
O-Aminobenzenesulfonic acid	ChEBI
O-Sulfanilic acid	ChEBI
Orthanilic acid	ChEBI
1-Aminobenzene-2-sulfonate	Generator
1-Aminobenzene-2-sulphonate	Generator
1-Aminobenzene-2-sulphonic acid	Generator
2-Sulfanilate	Generator
2-Sulphanilate	Generator
2-Sulphanilic acid	Generator
Aniline-O-sulfonate	Generator
Aniline-O-sulphonate	Generator
O-Aminobenzenesulfonate	Generator
O-Aminobenzenesulphonate	Generator
O-Aminobenzenesulphonic acid	Generator
O-Sulfanilate	Generator
O-Sulphanilate	Generator
O-Sulphanilic acid	Generator
Orthanilate	Generator
2-Aminobenzenesulfonate	Generator
2-Aminobenzenesulphonate	Generator
2-Aminobenzenesulphonic acid	Generator
ortho-Sulfanilic acid	MeSH

Chemical Formula

C₆H₇NO₃S

Average Molecular Weight

173.19

Monoisotopic Molecular Weight

173.014664263

IUPAC Name

2-aminobenzene-1-sulfonic acid

Traditional Name

orthanilic acid

CAS Registry Number

Not Available

SMILES

NC1=CC=CC=C1S(O)(=O)=O

InChI Identifier

InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)

InChI Key

ZMCHBSMFKQYNKA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonic acids and derivatives. These are organic compounds containing a sulfonic acid or a derivative thereof that is linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonic acids and derivatives

Direct Parent

Benzenesulfonic acids and derivatives

Alternative Parents

Substituents

Benzenesulfonate
Arylsulfonic acid or derivatives
Benzenesulfonyl group
1-sulfo,2-unsubstituted aromatic compound
Aniline or substituted anilines
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobenzenesulfonic acid (CHEBI:1015 )

Ontology

Not Available

Not Available

Not Available

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	-1.5	ALOGPS
logP	0.1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-3.7	ChemAxon
pKa (Strongest Basic)	2.33	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.38 m³·mol⁻¹	ChemAxon
Polarizability	15.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	137.895	32859911
AllCCS	[M+H-H2O]+	133.527	32859911
AllCCS	[M+Na]+	143.139	32859911
AllCCS	[M+NH4]+	141.966	32859911
AllCCS	[M-H]-	128.993	32859911
AllCCS	[M+Na-2H]-	130.39	32859911
AllCCS	[M+HCOO]-	131.98	32859911
DeepCCS	[M+H]+	129.02	30932474
DeepCCS	[M-H]-	125.189	30932474
DeepCCS	[M-2H]-	162.499	30932474
DeepCCS	[M+Na]+	138.024	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Aminobenzenesulfonic acid,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	1759.7	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	1621.8	Standard non polar	33892256
2-Aminobenzenesulfonic acid,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	2741.4	Standard polar	33892256
2-Aminobenzenesulfonic acid,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	1860.1	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	1668.0	Standard non polar	33892256
2-Aminobenzenesulfonic acid,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	2566.5	Standard polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C	1835.3	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C	1808.1	Standard non polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C	2277.3	Standard polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C	1846.7	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C	1888.8	Standard non polar	33892256
2-Aminobenzenesulfonic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C	2276.6	Standard polar	33892256
2-Aminobenzenesulfonic acid,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1838.4	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2024.7	Standard non polar	33892256
2-Aminobenzenesulfonic acid,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2123.5	Standard polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	2023.2	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	1862.4	Standard non polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N	2840.1	Standard polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	2109.7	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	1901.7	Standard non polar	33892256
2-Aminobenzenesulfonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O	2667.4	Standard polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C	2303.2	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C	2284.1	Standard non polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C	2451.1	Standard polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C(C)(C)C	2306.9	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C(C)(C)C	2336.9	Standard non polar	33892256
2-Aminobenzenesulfonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1S(=O)(=O)O)[Si](C)(C)C(C)(C)C	2407.0	Standard polar	33892256
2-Aminobenzenesulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2505.4	Semi standard non polar	33892256
2-Aminobenzenesulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2722.9	Standard non polar	33892256
2-Aminobenzenesulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2385.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 10V, Positive-QTOF	splash10-00di-0900000000-bc33080bd75eb70840dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 20V, Positive-QTOF	splash10-00dl-6900000000-75d8adba5bb09caf7deb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 40V, Positive-QTOF	splash10-0f6x-9000000000-d7e27b14a9a7b0b8d1af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 10V, Negative-QTOF	splash10-00di-1900000000-9713955a02454e40a0ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 20V, Negative-QTOF	splash10-006x-9600000000-49d7bcfe92bf637fcc87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 40V, Negative-QTOF	splash10-0006-9200000000-1e4c963b3e20c42ec39f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 10V, Positive-QTOF	splash10-00di-0900000000-bca02da82cb39c1aab70	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 20V, Positive-QTOF	splash10-00di-3900000000-4ad3a7d8eb2702db924a	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 40V, Positive-QTOF	splash10-0uxu-9000000000-11c2e6c1874747206c54	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 10V, Negative-QTOF	splash10-00di-0900000000-75084b2ead9ea6c4036a	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 20V, Negative-QTOF	splash10-00di-1900000000-22d440f57fd3468e1b75	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminobenzenesulfonic acid 40V, Negative-QTOF	splash10-014l-6900000000-8a80271a02c5dfa81965	2021-10-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

C06333

BioCyc ID

2-AMINOBENZENESULFONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6926

PDB ID

Not Available

ChEBI ID

1015

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

National Institute of Environmental Health Science (NIEHS) [Link]

Showing metabocard for 2-Aminobenzenesulfonic acid (HMDB0304940)

MOL for HMDB0304940 (2-Aminobenzenesulfonic acid)

3D MOL for HMDB0304940 (2-Aminobenzenesulfonic acid)

3D SDF for HMDB0304940 (2-Aminobenzenesulfonic acid)

3D-SDF for HMDB0304940 (2-Aminobenzenesulfonic acid)

PDB for HMDB0304940 (2-Aminobenzenesulfonic acid)

3D PDB for HMDB0304940 (2-Aminobenzenesulfonic acid)

SMILES for HMDB0304940 (2-Aminobenzenesulfonic acid)

INCHI for HMDB0304940 (2-Aminobenzenesulfonic acid)

Structure for HMDB0304940 (2-Aminobenzenesulfonic acid)

3D Structure for HMDB0304940 (2-Aminobenzenesulfonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra