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Showing NP-Card for sulfanilamide (NP0150632)

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Record Information
Version2.0
Created at2022-09-02 06:48:23 UTC
Updated at2022-09-02 06:48:23 UTC
NP-MRD IDNP0150632
Secondary Accession NumbersNone
Natural Product Identification
Common Namesulfanilamide
DescriptionSulfanilamide, also known as streptocide or sulfamine, 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. Sulfanilamide is a drug which is used for the treatment of vulvovaginitis caused by candida albicans. Sulfanilamide is a moderately basic compound (based on its pKa). sulfanilamide is found in Streptomyces lincolnensis. sulfanilamide was first documented in 2006 (PMID: 16997145). A sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-position (PMID: 22214209) (PMID: 22342371) (PMID: 22974493) (PMID: 23061287).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0150632 (sulfanilamide)

259
  Mrv0541 02231214332D          

 11 11  0  0  0  0            999 V2000
    2.4751    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.8250    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  4  1  0  0  0  0
  1  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0150632 (sulfanilamide)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.3677    0.7030    0.0442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819    0.3302    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743   -0.5318   -0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1273   -0.8748   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.3877    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -0.8355    0.2204 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.3669    0.2640   -0.7059 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355   -2.2020   -0.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790   -0.7305    1.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056    0.4774    1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    0.8157    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104    1.5512    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    0.1236   -0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -0.9333   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2859   -1.5532   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    0.1666   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1026    1.2596   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607    0.8655    1.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254    1.4921    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 10  1  0
 10 11  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  6  9  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
 10 18  1  0
 11 19  1  0
  7 16  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0150632 (sulfanilamide)

259
  Mrv0541 02231214332D          

 11 11  0  0  0  0            999 V2000
    2.4751    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.8250    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  4  1  0  0  0  0
  1  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(C=C1)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

> <INCHI_KEY>
FDDDEECHVMSUSB-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O2S

> <MOLECULAR_WEIGHT>
172.205

> <EXACT_MASS>
172.0306482

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.248819900649025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-aminobenzene-1-sulfonamide

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
-0.24964936833333337

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.990054903867138

> <JCHEM_PKA_STRONGEST_BASIC>
2.2653256426712796

> <JCHEM_POLAR_SURFACE_AREA>
86.17999999999999

> <JCHEM_REFRACTIVITY>
42.91630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfanilamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0150632 (sulfanilamide)

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PDB for NP0150632 (sulfanilamide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 259                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   2.310   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080   2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160   2.310   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.620   3.850   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.620  -3.850   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.620   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.286   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.954   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.620  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.286  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    6                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    9                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6   10                                                       
CONECT    8    6   11                                                       
CONECT    9    5   10   11                                                  
CONECT   10    7    9                                                       
CONECT   11    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0150632 (sulfanilamide)
Download
SMILES for NP0150632 (sulfanilamide)
NC1=CC=C(C=C1)S(N)(=O)=O
Download
INCHI for NP0150632 (sulfanilamide)
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
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View in JSmol
Synonyms
ValueSource
4-Aminobenzene sulfonic acid amideChEBI
4-AzanylbenzenesulfonamideChEBI
p-AminobenzenesulfamideChEBI
p-AminobenzenesulfonamideChEBI
Para-aminobenzenesulfonamideChEBI
Prontosil albumChEBI
SAChEBI
StreptocideChEBI
SulfamineChEBI
SulphanilamideChEBI
StreptocidKegg
AVCKegg
4-Aminobenzene sulfonate amideGenerator
4-Aminobenzene sulphonate amideGenerator
4-Aminobenzene sulphonic acid amideGenerator
4-AzanylbenzenesulphonamideGenerator
p-AminobenzenesulphamideGenerator
p-AminobenzenesulphonamideGenerator
Para-aminobenzenesulphonamideGenerator
SulphamineGenerator
p-AminobenzenesulfonylamideHMDB
p-AminobenzensulfonamideHMDB
p-AminophenylsulfonamideHMDB
p-AnilinesulfonamideHMDB
p-SulfamidoanilineHMDB
p-SulfamoylanilineHMDB
PABSHMDB
Sulfanilimidic acidHMDB
SulfonylamideHMDB
SulphonamideHMDB
Sulfanilamide cadmium saltHMDB
Sulfanilamide hydrochlorideHMDB
Sulfanilamide strontium saltHMDB
Sulfanilamide zinc saltHMDB
Sulfanilamide monohydrateHMDB
Azol polvoHMDB
Sulfanilamide magnesium saltHMDB
Sulfanilamide silver saltHMDB
Sulfanilamide sodium saltHMDB
4-AminobenzenesulfonamideHMDB
Sulfanilamide barium saltHMDB
Sulfanilamide lithium saltHMDB
Sulfanilamide sodiumHMDB
4 AminobenzenesulfonamideHMDB
Chemical FormulaC6H8N2O2S
Average Mass172.2050 Da
Monoisotopic Mass172.03065 Da
IUPAC Name4-aminobenzene-1-sulfonamide
Traditional Namesulfanilamide
CAS Registry NumberNot Available
SMILES
NC1=CC=C(C=C1)S(N)(=O)=O
InChI Identifier
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
InChI KeyFDDDEECHVMSUSB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces lincolnensisLOTUS Database
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzenesulfonamides  
Direct ParentAminobenzenesulfonamides  
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
    • 

  • Benzenesulfonyl group
    • 

  • Aniline or substituted anilines
    • 

  • Organosulfonic acid amide
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Organosulfonic acid or derivatives
    • 

  • Sulfonyl
    • 

  • Aminosulfonyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.16ALOGPS
logP-0.25ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.92 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014404  
DrugBank IDDB00259  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5142  
KEGG Compound IDC07458  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfanilamide  
METLIN IDNot Available
PubChem Compound5333  
PDB IDSAN  
ChEBI ID45373  
Good Scents IDNot Available
References
General References
  1. Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. doi: 10.1016/j.drudis.2006.08.003.  Epub 2006 Sep 7. [PubMed:16997145  ] 
  2. Maresca A, Scozzafava A, Vullo D, Supuran CT: Dihalogenated sulfanilamides and benzolamides are effective inhibitors of the three beta-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem. 2013 Apr;28(2):384-7. doi: 10.3109/14756366.2011.645539.  Epub 2012 Jan 3. [PubMed:22214209  ] 
  3. Eyanagi R, Toda A, Imoto M, Uchiyama H, Ishii Y, Kuroki H, Kuramoto Y, Soeda S, Shimeno H: Covalent binding of nitroso-sulfonamides to glutathione S-transferase in guinea pigs with delayed type hypersensitivity. Int Immunopharmacol. 2012 Apr;12(4):694-700. doi: 10.1016/j.intimp.2012.01.017.  Epub 2012 Feb 13. [PubMed:22342371  ] 
  4. Demirdag R, Comakli V, Senturk M, Ekinci D, Irfan Kufrevioglu O, Supuran CT: Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Bioorg Med Chem. 2013 Mar 15;21(6):1522-5. doi: 10.1016/j.bmc.2012.08.018. Epub  2012 Aug 24. [PubMed:22974493  ] 
  5. Zevzikoviene A, Zevzikovas A, Tarasevicius E, Pavlonis A, Dirse V: Synthesis and in vitro antimicrobial study of 4-thiazolidinone containing sulfanilamide. Acta Pol Pharm. 2012 Sep-Oct;69(5):911-5. [PubMed:23061287  ] 
  6. LOTUS database [Link]