NP-MRD: Showing NP-Card for sulfadiazine (NP0314931)

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Record Information

Version

2.0

Created at

2022-09-11 13:18:24 UTC

Updated at

2022-09-11 13:18:24 UTC

NP-MRD ID

NP0314931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sulfadiazine

Description

Sulfadiazine, also known as sulfapyrimidine or sulphadiazina, 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. Sulfadiazine is a drug which is used for the treatment of rheumatic fever and meningococcal meningitis. Sulfadiazine is a moderately basic compound (based on its pKa). sulfadiazine is found in Apis cerana. sulfadiazine was first documented in 1953 (PMID: 13037579). A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position (PMID: 12811231) (PMID: 15907564) (PMID: 18706672).

Structure

MOL 3D MOL SDF PDB SMILES InChI

359
  Mrv0541 02231214372D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.5404    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.6029    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  8  1  0  0  0  0
  4 14  1  0  0  0  0
  5 11  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  2  0  0  0  0
  7 14  2  0  0  0  0
  7 16  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0314931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

> <INCHI_KEY>
SEEPANYCNGTZFQ-UHFFFAOYSA-N

> <FORMULA>
C10H10N4O2S

> <MOLECULAR_WEIGHT>
250.277

> <EXACT_MASS>
250.052446274

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.391364892131367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
0.38726080800000007

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.989915444982717

> <JCHEM_PKA_STRONGEST_BASIC>
2.013677898293487

> <JCHEM_POLAR_SURFACE_AREA>
97.97

> <JCHEM_REFRACTIVITY>
64.20090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfadiazine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 359                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   1.009   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080   1.009   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160   1.009   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.620   2.549   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.620  -5.151   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.954   4.859   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.288   2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.620  -0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286  -1.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -1.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620  -3.611   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.286  -2.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954  -2.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   3.319   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.288   5.629   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   3.319   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.621   4.859   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    8                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1   14                                                       
CONECT    5   11                                                            
CONECT    6   14   15                                                       
CONECT    7   14   16                                                       
CONECT    8    1    9   10                                                  
CONECT    9    8   12                                                       
CONECT   10    8   13                                                       
CONECT   11    5   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
CONECT   14    4    6    7                                                  
CONECT   15    6   17                                                       
CONECT   16    7   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-Sulfanilamidopyrimidine	ChEBI
2-Sulfanilylaminopyrimidine	ChEBI
4-Amino-N-2-pyrimidinylbenzenesulfonamide	ChEBI
N(1)-2-Pyrimidinylsulfanilamide	ChEBI
N(1)-2-Pyrimidylsulfanilamide	ChEBI
Sulfadiazin	ChEBI
Sulfadiazina	ChEBI
Sulfadiazinum	ChEBI
Sulfapyrimidine	ChEBI
Sulphadiazine	ChEBI
2-Sulphanilamidopyrimidine	Generator
2-Sulphanilylaminopyrimidine	Generator
4-Amino-N-2-pyrimidinylbenzenesulphonamide	Generator
N(1)-2-Pyrimidinylsulphanilamide	Generator
N(1)-2-Pyrimidylsulphanilamide	Generator
Sulphadiazin	Generator
Sulphadiazina	Generator
Sulphadiazinum	Generator
Sulphapyrimidine	Generator
SDA	HMDB
Sulfadiazene	HMDB
Sulfanilamidopyrimidine	HMDB
Sulfapirimidin	HMDB
Sulfapyrimidin	HMDB
Sulfazin	HMDB
Zinc sulfadiazine	HMDB
Sulfadiazine, zinc	HMDB
Sulfazine	HMDB

Chemical Formula

C₁₀H₁₀N₄O₂S

Average Mass

250.2770 Da

Monoisotopic Mass

250.05245 Da

IUPAC Name

4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide

Traditional Name

sulfadiazine

CAS Registry Number

Not Available

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1

InChI Identifier

InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

InChI Key

SEEPANYCNGTZFQ-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
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

substituted aniline (CHEBI:9328 )
sulfonamide (CHEBI:9328 )
pyrimidines (CHEBI:9328 )
sulfonamide antibiotic (CHEBI:9328 )

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	0.25	ALOGPS
logP	0.39	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.2 m³·mol⁻¹	ChemAxon
Polarizability	24.39 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

HMDB0014503

DrugBank ID

DB00359

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010662

KNApSAcK ID

Not Available

Chemspider ID

5026

KEGG Compound ID

C07658

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfadiazine

METLIN ID

Not Available

PubChem Compound

5215

PDB ID

Not Available

ChEBI ID

9328

Good Scents ID

Not Available

References

General References

Perazella MA: Drug-induced renal failure: update on new medications and unique mechanisms of nephrotoxicity. Am J Med Sci. 2003 Jun;325(6):349-62. doi: 10.1097/00000441-200306000-00006. [PubMed:12811231 ]
LEHR D, TERRANOVA R, BLUMENFELD S, GOLDFARB ML: Therapy with a new sulfonamide triple mixture; sulfadiazine, sulfamerazine, elkosin. Postgrad Med. 1953 Mar;13(3):231-38. doi: 10.1080/00325481.1953.11711317. [PubMed:13037579 ]
Elandalloussi LM, Rodrigues PM, Afonso R, Leite RB, Nunes PA, Cancela ML: Shikimate and folate pathways in the protozoan parasite, Perkinsus olseni. Mol Biochem Parasitol. 2005 Jul;142(1):106-9. doi: 10.1016/j.molbiopara.2005.03.014. Epub 2005 Apr 8. [PubMed:15907564 ]
Sukul P, Lamshoft M, Zuhlke S, Spiteller M: Sorption and desorption of sulfadiazine in soil and soil-manure systems. Chemosphere. 2008 Nov;73(8):1344-50. doi: 10.1016/j.chemosphere.2008.06.066. Epub 2008 Aug 15. [PubMed:18706672 ]
LOTUS database [Link]

Showing NP-Card for sulfadiazine (NP0314931)

MOL for NP0314931 (sulfadiazine)

3D MOL for NP0314931 (sulfadiazine)

3D SDF for NP0314931 (sulfadiazine)

3D-SDF for NP0314931 (sulfadiazine)

PDB for NP0314931 (sulfadiazine)

3D PDB for NP0314931 (sulfadiazine)

SMILES for NP0314931 (sulfadiazine)

INCHI for NP0314931 (sulfadiazine)

Structure for NP0314931 (sulfadiazine)

3D Structure for NP0314931 (sulfadiazine)