NP-MRD: Showing NP-Card for Metosulam (NP0337449)

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Record Information

Version

2.0

Created at

2024-09-11 10:54:48 UTC

Updated at

2024-09-11 10:54:49 UTC

NP-MRD ID

NP0337449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metosulam

Description

Metosulam, also known as DE 511, belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position. Metosulam is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308052D          

 26 28  0  0  0  0            999 V2000
   -3.4712    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.0940    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  9  2  0  0  0  0
 17 13  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 14  2  0  0  0  0
 20 12  1  0  0  0  0
 21 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 25  3  1  0  0  0  0
 25 10  1  0  0  0  0
 26 14  1  0  0  0  0
 26 20  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  2  0  0  0  0
M  END


  Mrv0541 05061308052D          

 26 28  0  0  0  0            999 V2000
   -3.4712    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.0940    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  9  2  0  0  0  0
 17 13  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 14  2  0  0  0  0
 20 12  1  0  0  0  0
 21 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 25  3  1  0  0  0  0
 25 10  1  0  0  0  0
 26 14  1  0  0  0  0
 26 20  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C14H13Cl2N5O4S/c1-7-4-5-8(15)12(11(7)16)20-26(22,23)14-18-13-17-9(24-2)6-10(25-3)21(13)19-14/h4-6,20H,1-3H3

> <INCHI_KEY>
VGHPMIFEKOFHHQ-UHFFFAOYSA-N

> <FORMULA>
C14H13Cl2N5O4S

> <MOLECULAR_WEIGHT>
418.255

> <EXACT_MASS>
417.006530033

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
39.17116260867917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.468920647666666

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.793961967534287

> <JCHEM_PKA_STRONGEST_BASIC>
-3.48465767796038

> <JCHEM_POLAR_SURFACE_AREA>
107.71000000000001

> <JCHEM_REFRACTIVITY>
107.52709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metosulam

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.480   0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.170  -1.158   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.630  -1.158   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.940   0.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.860   0.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.170   1.509   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -0.320   0.175   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0      -4.940   2.843   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -1.860   2.843   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -0.320   1.303   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.320   4.383   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0      -0.320   2.843   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    9   10                                                       
CONECT    7    1    4   11                                                  
CONECT    8    5   12   15                                                  
CONECT    9    6   17   24                                                  
CONECT   10    6   21   25                                                  
CONECT   11    7   12   16                                                  
CONECT   12    8   11   20                                                  
CONECT   13   17   18   21                                                  
CONECT   14   18   19   26                                                  
CONECT   15    8                                                            
CONECT   16   11                                                            
CONECT   17    9   13                                                       
CONECT   18   13   14                                                       
CONECT   19   14   21                                                       
CONECT   20   12   26                                                       
CONECT   21   10   13   19                                                  
CONECT   22   26                                                            
CONECT   23   26                                                            
CONECT   24    2    9                                                       
CONECT   25    3   10                                                       
CONECT   26   14   20   22   23                                             
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
DE 511	HMDB
N-(2,6-Dichloro-3-methylphenyl)-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide, 9ci	HMDB
XDE 511	HMDB
XRD 511	HMDB
N-(2,6-Dichloro-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo-(1,5a)-pyrimidine-2-sulfonamide	MeSH

Chemical Formula

C₁₄H₁₃Cl₂N₅O₄S

Average Mass

418.2550 Da

Monoisotopic Mass

417.00653 Da

IUPAC Name

N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

Traditional Name

metosulam

CAS Registry Number

Not Available

SMILES

COC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl

InChI Identifier

InChI=1S/C14H13Cl2N5O4S/c1-7-4-5-8(15)12(11(7)16)20-26(22,23)14-18-13-17-9(24-2)6-10(25-3)21(13)19-14/h4-6,20H,1-3H3

InChI Key

VGHPMIFEKOFHHQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazolopyrimidines

Sub Class

1,2,4-triazolopyrimidine-2-sulfonamides

Direct Parent

1,2,4-triazolopyrimidine-2-sulfonanilides

Alternative Parents

Substituents

1,2,4-triazolopyrimidine-2-sulfonanilide
Sulfanilide
1,3-dichlorobenzene
Alkyl aryl ether
Chlorobenzene
Halobenzene
Toluene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Pyrimidine
Organosulfonic acid amide
Azole
Heteroaromatic compound
Aminosulfonyl compound
1,2,4-triazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Triazole
Sulfonyl
Azacycle
Ether
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:82024 )
Anilide herbicides (C18867 )

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	3.76	ALOGPS
logP	3.47	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.79	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	107.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.53 m³·mol⁻¹	ChemAxon
Polarizability	39.17 Å³	ChemAxon
Number of Rings	3	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

HMDB0034850

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013416

KNApSAcK ID

Not Available

Chemspider ID

77938

KEGG Compound ID

C18867

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Metosulam (NP0337449)

MOL for NP0337449 (Metosulam)

3D MOL for NP0337449 (Metosulam)

3D SDF for NP0337449 (Metosulam)

3D-SDF for NP0337449 (Metosulam)

PDB for NP0337449 (Metosulam)

3D PDB for NP0337449 (Metosulam)

SMILES for NP0337449 (Metosulam)

INCHI for NP0337449 (Metosulam)

Structure for NP0337449 (Metosulam)

3D Structure for NP0337449 (Metosulam)