NP-MRD: Showing NP-Card for n-(4-aminobenzenesulfonyl)ethanimidic acid (NP0250439)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 13:15:31 UTC

Updated at

2022-09-07 13:15:31 UTC

NP-MRD ID

NP0250439

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(4-aminobenzenesulfonyl)ethanimidic acid

Description

Sulfacetamide, also known as sulphacetamidum or acetosulfamine, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Sulfacetamide is a drug which is used for the treatment of bacterial vaginitis, keratitis, acute conjunctivitis, and blepharitis. Sulfacetamide is a moderately basic compound (based on its pKa). n-(4-aminobenzenesulfonyl)ethanimidic acid is found in Apis cerana. n-(4-aminobenzenesulfonyl)ethanimidic acid was first documented in 1992 (PMID: 1578876). A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen (PMID: 14959943) (PMID: 15224788) (PMID: 21486528).

Structure

MOL 3D MOL SDF PDB SMILES InChI

634
  Mrv0541 02231214502D          

 14 14  0  0  0  0            999 V2000
    2.4751    0.7466    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    1.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.5717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.5534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  4 13  2  0  0  0  0
  5 13  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250439

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)

> <INCHI_KEY>
SKIVFJLNDNKQPD-UHFFFAOYSA-N

> <FORMULA>
C8H10N2O3S

> <MOLECULAR_WEIGHT>
214.242

> <EXACT_MASS>
214.041212886

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.491204809580424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-aminobenzenesulfonyl)acetamide

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-0.2610410626666669

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.299983698566216

> <JCHEM_PKA_STRONGEST_BASIC>
2.1375402711797

> <JCHEM_POLAR_SURFACE_AREA>
89.26

> <JCHEM_REFRACTIVITY>
52.482200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfacetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 634                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   1.394   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080   1.394   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160   1.394   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.288   2.934   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   2.934   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.620  -4.766   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.620  -0.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.286  -0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954  -0.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -3.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.286  -2.456   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954  -2.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954   3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   5.244   0.000  0.00  0.00           C+0
CONECT    1    2    3    5    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   13                                                            
CONECT    5    1   13                                                       
CONECT    6   10                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    7   12                                                       
CONECT   10    6   11   12                                                  
CONECT   11    8   10                                                       
CONECT   12    9   10                                                       
CONECT   13    4    5   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Acetosulfamine	ChEBI
N'-acetylsulfanilamide	ChEBI
N-((p-Aminophenyl)sulfonyl)acetamide	ChEBI
N-(p-Aminobenzenesulfonyl)acetamide	ChEBI
N-[(p-Aminophenyl)sulfonyl]acetamide	ChEBI
N-Acetyl-4-aminobenzenesulfonamide	ChEBI
N-Acetylsulfanilamide	ChEBI
N-Sulfanilylacetamide	ChEBI
N-Sulphanilylacetamide	ChEBI
N(1)-Acetyl-4-aminophenylsulfonamide	ChEBI
N(1)-Acetylsulfanilamide	ChEBI
p-Aminobenzenesulfonacetamide	ChEBI
p-Aminobenzenesulfonoacetamide	ChEBI
Sulfacetamida	ChEBI
Sulfacetamidum	ChEBI
Sulfanilazetamid	ChEBI
Sulphacetamide	ChEBI
Sulphacetamidum	ChEBI
Acetosulphamine	Generator
N'-acetylsulphanilamide	Generator
N-((p-Aminophenyl)sulphonyl)acetamide	Generator
N-(p-Aminobenzenesulphonyl)acetamide	Generator
N-[(p-Aminophenyl)sulphonyl]acetamide	Generator
N-Acetyl-4-aminobenzenesulphonamide	Generator
N-Acetylsulphanilamide	Generator
N(1)-Acetyl-4-aminophenylsulphonamide	Generator
N(1)-Acetylsulphanilamide	Generator
p-Aminobenzenesulphonacetamide	Generator
p-Aminobenzenesulphonoacetamide	Generator
Sulphacetamida	Generator
Sulphanilazetamid	Generator
AK-sulf	HMDB
Ceta sulfa	HMDB
Monosodium salt, sulfacetamide	HMDB
Sodium, sulfacetamide	HMDB
Sulf-10	HMDB
Sulfacetamida, colircusi	HMDB
Sulfacetamide sodium	HMDB
Sulfacetamide, monosodium salt, anhydrous	HMDB
Sulfacyl	HMDB
Sulfair	HMDB
Acetopt	HMDB
Albucid	HMDB
Belph 10	HMDB
Bleph	HMDB
Sodium sulamyd	HMDB
Sulf 10	HMDB
Sulfacetam, coliriocilina	HMDB
Acetylsulfanilamide	HMDB
Antébor	HMDB
Coliriocilina sulfacetam	HMDB
AK sulf	HMDB
Belph-10	HMDB
Cetamide	HMDB
Colircusi sulfacetamida	HMDB
Isopto cetamide	HMDB
Sulamyd, sodium	HMDB
Sulfacetamide monosodium salt	HMDB
Sulfacil	HMDB

Chemical Formula

C₈H₁₀N₂O₃S

Average Mass

214.2420 Da

Monoisotopic Mass

214.04121 Da

IUPAC Name

N-(4-aminobenzenesulfonyl)acetamide

Traditional Name

sulfacetamide

CAS Registry Number

Not Available

SMILES

CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)

InChI Key

SKIVFJLNDNKQPD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Acetamide
Aminosulfonyl compound
Amino acid or derivatives
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:63845 )
sulfonamide (CHEBI:63845 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.15	ALOGPS
logP	-0.26	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	2.14	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	1	ChemAxon
Refractivity	52.48 m³·mol⁻¹	ChemAxon
Polarizability	20.49 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

External Links

HMDB ID

HMDB0014772

DrugBank ID

DB00634

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfacetamide

METLIN ID

Not Available

PubChem Compound

5320

PDB ID

Not Available

ChEBI ID

63845

Good Scents ID

Not Available

References

General References

Roth HW, Leimbeck R, Sonnenschein B, Anger CB, Weber S: [The effective antibacterial spectrum of sulfacetamide]. Klin Monbl Augenheilkd. 1992 Mar;200(3):182-6. doi: 10.1055/s-2008-1045735. [PubMed:1578876 ]
Del Rosso JQ: Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations. Cutis. 2004 Jan;73(1 Suppl):29-33. [PubMed:14959943 ]
Hull CA, Johnson SM: A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor. Cutis. 2004 Jun;73(6):425-9. [PubMed:15224788 ]
Mandal B, Alexander KS, Riga AT: Sulfacetamide loaded Eudragit(R) RL100 nanosuspension with potential for ocular delivery. J Pharm Pharm Sci. 2010;13(4):510-23. [PubMed:21486528 ]
LOTUS database [Link]

Showing NP-Card for n-(4-aminobenzenesulfonyl)ethanimidic acid (NP0250439)

MOL for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

3D MOL for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

3D SDF for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

3D-SDF for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

PDB for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

3D PDB for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

SMILES for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

INCHI for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

Structure for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)

3D Structure for NP0250439 (n-(4-aminobenzenesulfonyl)ethanimidic acid)