NP-MRD: Showing NP-Card for 2,2'-Dithiobis(pyridine N-oxide) (NP0080375)

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Record Information

Version

2.0

Created at

2022-04-29 01:24:12 UTC

Updated at

2022-04-29 01:24:12 UTC

NP-MRD ID

NP0080375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2'-Dithiobis(pyridine N-oxide)

Description

Dipyrithione, also known as omadine disulfide or omadine MDS, belongs to the class of organic compounds known as pyridinium derivatives. Pyridinium derivatives are compounds containing a pyridinium ring, which is the cationic form of pyridine. This drug decreases or eliminates dandruff from the scalp, which is caused by various types of fungi ,. The drug was marketed under the name Crimanex in the form of shampoo for the treatment of dandruff, however it is no longer available on the manufacturer website (Drossa Pharm. Fungicide, also called antimycotic, any toxic substance used to kill or inhibit the growth of fungi. Dipyrithione is an extremely weak basic (essentially neutral) compound (based on its pKa). It may be combined with other ingredients, such as triclosan to serve as antifungal and antibacterial skin treatments. It is currently used as a pesticide. Pyrithione derivatives, such as and sodium pyrithione, are widely used as cosmetic preservatives and as anti-dandruff agents in shampoos. Interestingly, dipyrithione has been studied and shown to have cytotoxic and potent broad-spectrum antitumor activity, which suggests a potential basis for an anticancer drug development. Dipyrithione is a pyrithione derivate used as bactericide and fungicide. Dandruff is a common scalp disease affecting >40% of the world's adult population, and may be caused by fungi such as _Malassezia globosa_ and _M. 2,2'-Dithiobis(pyridine N-oxide) is found in Allium stipitatum, Cortinarius and Cortinarius sp. . This drug is a fungicidal agent ,.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520002D          

 16 17  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  3  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
    0.7145   -3.7125    0.0000 C   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
    0.0000   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 S   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
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  5  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  CHG  4   1  -1   2   1  15   1  16  -1
M  END
> <DATABASE_ID>
NP0080375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H

> <INCHI_KEY>
ZHDBTKPXEJDTTQ-UHFFFAOYSA-N

> <FORMULA>
C10H8N2O2S2

> <MOLECULAR_WEIGHT>
252.31

> <EXACT_MASS>
252.002719854

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
23.20902373352692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.4398985293333333

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.2505865766249594

> <JCHEM_POLAR_SURFACE_AREA>
53.879999999999995

> <JCHEM_REFRACTIVITY>
63.2776

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+1
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  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       0.000  -4.620   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0      -1.334  -5.390   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+1
HETATM   16  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Bis(2-pyridyl-1-oxide)disulfide magnesium sulfate	MeSH
Omadine disulfide	MeSH
2,2'-Dithio-bis-pyridine-1-oxide magnesium sulfate	MeSH
Omadine MDS	MeSH
Dipyrithione magnesium sulfate	MeSH
OMDS	ChEMBL
2-[(1-oxo-1Λ⁵-pyridin-2-yl)disulphanyl]-1λ⁵-pyridin-1-one	Generator

Chemical Formula

C₁₀H₈N₂O₂S₂

Average Mass

252.3100 Da

Monoisotopic Mass

252.00272 Da

IUPAC Name

2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

Traditional Name

2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

CAS Registry Number

Not Available

SMILES

[O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-]

InChI Identifier

InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H

InChI Key

ZHDBTKPXEJDTTQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Allium stipitatum	Plant	KNApSAcK
Cortinarius	LOTUS Database	35616633
Cortinarius sp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinium derivatives. Pyridinium derivatives are compounds containing a pyridinium ring, which is the cationic form of pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinium derivatives

Direct Parent

Pyridinium derivatives

Alternative Parents

Substituents

Pyridinium
Heteroaromatic compound
Organic disulfide
Azacycle
Sulfenyl compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.5	ALOGPS
logP	-0.44	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.28 m³·mol⁻¹	ChemAxon
Polarizability	23.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB11327

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3109

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,2'-Dithiobis(pyridine N-oxide) (NP0080375)

MOL for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

3D MOL for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

3D SDF for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

3D-SDF for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

PDB for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

3D PDB for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

SMILES for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

INCHI for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

Structure for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))

3D Structure for NP0080375 (2,2'-Dithiobis(pyridine N-oxide))