NP-MRD: Showing NP-Card for Pallidin (NP0070275)

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Record Information

Version

2.0

Created at

2022-04-28 15:34:52 UTC

Updated at

2022-04-28 15:34:52 UTC

NP-MRD ID

NP0070275

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pallidin

Description

Sulfaperin, also known as sulphaperina or anastaf, 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. Sulfaperin is a moderately basic compound (based on its pKa). Pallidin is found in Rhaphisia pallida. Pallidin was first documented in 1962 (PMID: 14456012). A substituted aniline that is sulfanilamide in which on of the hydrogens of the sulfonamide group has been replaced by a 5-methylpyrimidin-2-yl group (PMID: 13998307) (PMID: 22279018).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.3898   -1.8129   -0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.9159    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4263   -0.6275    1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.1854    2.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    0.7829    1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    1.6425    1.9679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526    2.3907    1.0549 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4422    3.3640    1.8916 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    3.1258   -0.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7284    1.2267    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951    0.8141   -0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -0.1098   -1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913   -0.6282   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2217   -1.5768   -1.5745 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -0.2174    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    0.6990    0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999    0.5097    0.0352 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985   -0.3079   -0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808   -2.2923   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2418   -1.1876   -0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952   -2.5723    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -1.0897    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    1.8317    2.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    1.2037   -1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -0.4363   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893   -2.6011   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8871   -1.2998   -2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4777   -0.6408    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    1.0334    2.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3320   -0.4935   -1.5858 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  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
M  END


  Mrv1572004221607012D          

 18 19  0  0  0  0            999 V2000
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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
    3.5724    3.7125    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    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    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    4.1250    0.0000 C   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    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 18 10  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0070275

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CN=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N4O2S/c1-8-6-13-11(14-7-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

> <INCHI_KEY>
DZQVFHSCSRACSX-UHFFFAOYSA-N

> <FORMULA>
C11H12N4O2S

> <MOLECULAR_WEIGHT>
264.3

> <EXACT_MASS>
264.068096816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.96331016370892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(5-methylpyrimidin-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.9006821973333332

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.03437335545577

> <JCHEM_PKA_STRONGEST_BASIC>
2.0216854424164006

> <JCHEM_POLAR_SURFACE_AREA>
97.97

> <JCHEM_REFRACTIVITY>
69.24210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pallidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   5.390   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       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335   3.080   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.001  13.090   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       2.667  10.780   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       5.335  10.780   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       3.795   9.240   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.875   9.240   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       5.335   9.240   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    8   13                                                       
CONECT    7    8   14                                                       
CONECT    8    1    6    7                                                  
CONECT    9    2    3   12                                                  
CONECT   10    4    5   18                                                  
CONECT   11   13   14   15                                                  
CONECT   12    9                                                            
CONECT   13    6   11                                                       
CONECT   14    7   11                                                       
CONECT   15   11   18                                                       
CONECT   16   18                                                            
CONECT   17   18                                                            
CONECT   18   10   15   16   17                                             
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-(p-Aminobenzenesulfonamido)-5-methylpyrimidine	ChEBI
2-(Sulfanilamido)-5-methylpyrimidine	ChEBI
4-Amino-N-(5-methyl-2-pyrimidinyl)benzenesulfonamide	ChEBI
5-Methylsulfadiazine	ChEBI
Anastaf	ChEBI
Archisulfa	ChEBI
Avissul	ChEBI
Chemiopen	ChEBI
Demosulfan	ChEBI
Durisan	ChEBI
Isosulfamerazine	ChEBI
Methylsulfadiazine	ChEBI
N(1)-(5-Methyl-2-pyrimidinyl)sulfanilamide	ChEBI
Sulfaperina	ChEBI
Sulfaperinum	ChEBI
2-(p-Aminobenzenesulphonamido)-5-methylpyrimidine	Generator
2-(Sulphanilamido)-5-methylpyrimidine	Generator
4-Amino-N-(5-methyl-2-pyrimidinyl)benzenesulphonamide	Generator
5-Methylsulphadiazine	Generator
Archisulpha	Generator
Demosulphan	Generator
Isosulphamerazine	Generator
Methylsulphadiazine	Generator
N(1)-(5-Methyl-2-pyrimidinyl)sulphanilamide	Generator
Sulphaperina	Generator
Sulphaperinum	Generator
Sulphaperin	Generator
4-amino-N-(5-Methylpyrimidin-2-yl)benzenesulphonamide	Generator
Sulfaperine	MeSH
Sulfene	MeSH

Chemical Formula

C₁₁H₁₂N₄O₂S

Average Mass

264.3000 Da

Monoisotopic Mass

264.06810 Da

IUPAC Name

4-amino-N-(5-methylpyrimidin-2-yl)benzene-1-sulfonamide

Traditional Name

pallidin

CAS Registry Number

Not Available

SMILES

CC1=CN=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=C1

InChI Identifier

InChI=1S/C11H12N4O2S/c1-8-6-13-11(14-7-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

InChI Key

DZQVFHSCSRACSX-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
Rhaphisia pallida	-	KNApSAcK

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
Pyrimidine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen 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	0.41	ALOGPS
logP	0.9	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.03	ChemAxon
pKa (Strongest Basic)	2.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.24 m³·mol⁻¹	ChemAxon
Polarizability	25.96 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

DB13320

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

Sulfaperin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

131722

Good Scents ID

Not Available

References

General References

WAHLIG H: [Antibacterial properties of 5-methylsulfadiazine and phenoxymethylpenicillin in combined use and in the presence of penicillinase]. Wien Med Wochenschr. 1963 Feb 2;113:120-4. [PubMed:13998307 ]
KIMMIG J, MEYER-ROHN J: [Clinical and experimental studies on the chemotherapeutic effectiveness of sulfadiazines substituted in position 5 and the combination of 5-methylsulfadiazine with a derivative of penicillin]. Med Klin. 1962 Aug 24;57:1437-42. [PubMed:14456012 ]
Barry SJ, Wolff JC: Identification of isobaric amino-sulfonamides without prior separation. Rapid Commun Mass Spectrom. 2012 Feb 29;26(4):419-29. doi: 10.1002/rcm.6118. [PubMed:22279018 ]

Showing NP-Card for Pallidin (NP0070275)

MOL for NP0070275 (Pallidin)

3D MOL for NP0070275 (Pallidin)

3D SDF for NP0070275 (Pallidin)

3D-SDF for NP0070275 (Pallidin)

PDB for NP0070275 (Pallidin)

3D PDB for NP0070275 (Pallidin)

SMILES for NP0070275 (Pallidin)

INCHI for NP0070275 (Pallidin)

Structure for NP0070275 (Pallidin)

3D Structure for NP0070275 (Pallidin)