NP-MRD: Showing NP-Card for prontosil (NP0289093)

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Record Information

Version

2.0

Created at

2022-09-09 19:07:07 UTC

Updated at

2022-09-09 19:07:07 UTC

NP-MRD ID

NP0289093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

prontosil

Description

Prontosil, also known as prontosil rubrum or rubiazol, belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. Prontosil is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. prontosil is found in Apis cerana. prontosil was first documented in 2021 (PMID: 33506266). Based on a literature review a small amount of articles have been published on prontosil (PMID: 35909328) (PMID: 35163939) (PMID: 35156802) (PMID: 33231147).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -6.5840    1.1082   -0.0673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1702    0.9811   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3781    2.0848    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    1.9473    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3723    0.7486   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9516    0.7317    0.0365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613   -0.3177    0.1343 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559   -0.3436    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9490    0.7648    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449    0.6648    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -0.5581    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6985   -0.6391    0.2810 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.4019   -0.4172   -1.2568 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245    0.4399    1.1997 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754   -1.9525    0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683   -1.6797    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.5570    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1532   -0.3588   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5068   -1.5844   -0.4987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424   -0.2190   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0206    2.0420   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2164    0.2861    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    3.0443    0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    2.8322    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716    1.7189    0.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9694    1.5330    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7724   -1.3230   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559    0.3049   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -2.6353   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -2.4419   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927   -1.7612   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -2.3519    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1454   -1.0924   -0.4812 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 16  1  0
 16 17  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 12 15  2  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
 16 29  1  0
 17 30  1  0
 13 27  1  0
 13 28  1  0
 19 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv1652309092221072D          

 20 21  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -9.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(\N=N\C2=CC=C(C=C2)S(N)(=O)=O)C(N)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)/b17-16+

> <INCHI_KEY>
ABBQGOCHXSPKHJ-WUKNDPDISA-N

> <FORMULA>
C12H13N5O2S

> <MOLECULAR_WEIGHT>
291.33

> <EXACT_MASS>
291.078995853

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.5688611937561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]benzene-1-sulfonamide

> <JCHEM_LOGP>
1.3273183510000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.05951508607585

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.028823229344981

> <JCHEM_PKA_STRONGEST_BASIC>
3.4329273289807527

> <JCHEM_POLAR_SURFACE_AREA>
136.92

> <JCHEM_REFRACTIVITY>
81.93570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
prontosil

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.001 -10.010   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0       4.001 -16.170   0.000  0.00  0.00           S+0
HETATM   13  N   UNK     0       4.001 -17.710   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       2.461 -16.170   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.541 -16.170   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.000  -7.700   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17                                                       
CONECT   17   16    8                                                       
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
p-((2,4-Diaminophenyl)azo)benzenesulphonamide	ChEBI
Prontosil rubrum	ChEBI
Rubiazol	ChEBI
Sulfamidochrysoidine	ChEBI
Aseptil rojo	Kegg
p-((2,4-Diaminophenyl)azo)benzenesulfonamide	Generator
Sulphamidochrysoidine	Generator

Chemical Formula

C₁₂H₁₃N₅O₂S

Average Mass

291.3300 Da

Monoisotopic Mass

291.07900 Da

IUPAC Name

4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]benzene-1-sulfonamide

Traditional Name

prontosil

CAS Registry Number

Not Available

SMILES

NC1=CC=C(\N=N\C2=CC=C(C=C2)S(N)(=O)=O)C(N)=C1

InChI Identifier

InChI=1S/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)/b17-16+

InChI Key

ABBQGOCHXSPKHJ-WUKNDPDISA-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 azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

Alternative Parents

Substituents

Azobenzene
Benzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Monocyclic benzene moiety
Benzenoid
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonamide (CHEBI:8464 )
azobenzenes (CHEBI:8464 )

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	1.33	ChemAxon
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	3.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.94 m³·mol⁻¹	ChemAxon
Polarizability	29.57 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

60257

KEGG Compound ID

C07573

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prontosil

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8464

Good Scents ID

Not Available

References

General References

Youssrey A, Hegazy MA, Morsi A, Essam HM: Development and Validation of Green Chromatographic Approaches for Simultaneous Determination of Aspirin, Rosuvastatin and Clopidogrel in their Tertiary Mixture. J Chromatogr Sci. 2022 Jul 31:bmac058. doi: 10.1093/chromsci/bmac058. [PubMed:35909328 ]
Almalki AJ, Ibrahim TS, Taher ES, Mohamed MFA, Youns M, Hegazy WAH, Al-Mahmoudy AMM: Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides. Molecules. 2022 Jan 20;27(3):671. doi: 10.3390/molecules27030671. [PubMed:35163939 ]
Pachisia S, Gupta R, Gupta R: Molecular Assemblies Offering Hydrogen-Bonding Cavities: Influence of Macrocyclic Cavity and Hydrogen Bonding on Dye Adsorption. Inorg Chem. 2022 Feb 28;61(8):3616-3630. doi: 10.1021/acs.inorgchem.1c03747. Epub 2022 Feb 14. [PubMed:35156802 ]
Hassib ST, Hashem HMA, Mahrouse MA, Mostafa EA: Development and Bio-Analytical Validation of Chromatographic Determination Method of Rufinamide in Presence of its Metabolite in Human Plasma. J Chromatogr Sci. 2021 Apr 21;59(5):458-464. doi: 10.1093/chromsci/bmaa142. [PubMed:33506266 ]
Khan MN, Parmar DK, Das D: Recent Applications of Azo Dyes: A Paradigm Shift from Medicinal Chemistry to Biomedical Sciences. Mini Rev Med Chem. 2021;21(9):1071-1084. doi: 10.2174/1389557520999201123210025. [PubMed:33231147 ]
LOTUS database [Link]

Showing NP-Card for prontosil (NP0289093)

MOL for NP0289093 (prontosil)

3D MOL for NP0289093 (prontosil)

3D SDF for NP0289093 (prontosil)

3D-SDF for NP0289093 (prontosil)

PDB for NP0289093 (prontosil)

3D PDB for NP0289093 (prontosil)

SMILES for NP0289093 (prontosil)

INCHI for NP0289093 (prontosil)

Structure for NP0289093 (prontosil)

3D Structure for NP0289093 (prontosil)