NP-MRD: Showing NP-Card for Cloransulam-methyl (NP0337107)

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Record Information

Version

2.0

Created at

2024-09-11 09:20:24 UTC

Updated at

2024-09-11 09:20:24 UTC

NP-MRD ID

NP0337107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cloransulam-methyl

Description

Cloransulam-methyl, also known as DE 565 or first Rate, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Cloransulam-methyl is an extremely weak basic (essentially neutral) compound (based on its pKa). It is not approved for use within the European Area. The methyl ester of cloransulam. Cloransulam-methyl was first documented in 2000 (PMID: 10888581). An inhibitor of acetohydroxyacid synthase (AHAS), it prevents the synthesis of amino acids in plants and is used as a herbicide for the control of post-emergence control of broad-leaved weeds in soybeans (PMID: 11128225) (PMID: 26884355).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306572D          

 28 30  0  0  0  0            999 V2000
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.9519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 10  1  0  0  0  0
 18 15  2  0  0  0  0
 19 11  2  0  0  0  0
 19 14  1  0  0  0  0
 20 14  2  0  0  0  0
 21 12  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
 22 20  1  0  0  0  0
 23 13  2  0  0  0  0
 26  2  1  0  0  0  0
 26 13  1  0  0  0  0
 27  3  1  0  0  0  0
 27 15  1  0  0  0  0
 28 14  1  0  0  0  0
 28 21  1  0  0  0  0
 28 24  2  0  0  0  0
 28 25  2  0  0  0  0
M  END


  Mrv0541 05061306572D          

 28 30  0  0  0  0            999 V2000
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.9519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 10  1  0  0  0  0
 18 15  2  0  0  0  0
 19 11  2  0  0  0  0
 19 14  1  0  0  0  0
 20 14  2  0  0  0  0
 21 12  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
 22 20  1  0  0  0  0
 23 13  2  0  0  0  0
 26  2  1  0  0  0  0
 26 13  1  0  0  0  0
 27  3  1  0  0  0  0
 27 15  1  0  0  0  0
 28 14  1  0  0  0  0
 28 21  1  0  0  0  0
 28 24  2  0  0  0  0
 28 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1=NC(F)=CC2=NC(=NN12)S(=O)(=O)NC1=C(C=CC=C1Cl)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C15H13ClFN5O5S/c1-3-27-15-18-10(17)7-11-19-14(20-22(11)15)28(24,25)21-12-8(13(23)26-2)5-4-6-9(12)16/h4-7,21H,3H2,1-2H3

> <INCHI_KEY>
BIKACRYIQSLICJ-UHFFFAOYSA-N

> <FORMULA>
C15H13ClFN5O5S

> <MOLECULAR_WEIGHT>
429.811

> <EXACT_MASS>
429.030995153

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.657804492096005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-chloro-2-{5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamido}benzoate

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.1604452253333326

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.05207309727954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0075673498877764

> <JCHEM_POLAR_SURFACE_AREA>
124.78

> <JCHEM_REFRACTIVITY>
108.47219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cloransulam

> <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       3.864   8.233   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.643   1.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.563   6.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.333   5.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.023   6.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.563   4.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.253   5.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.333   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -2.713   5.510   0.000  0.00  0.00          Cl+0
HETATM   17  F   UNK     0       5.198   1.303   0.000  0.00  0.00           F+0
HETATM   18  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -4.253   2.843   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       1.197   3.613   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      -6.563   1.509   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.713   4.383   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.713   1.303   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.873   2.843   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0      -2.713   2.843   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2   26                                                            
CONECT    3    1   27                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    5   12   13                                                  
CONECT    9    6   12   16                                                  
CONECT   10    7   17   18                                                  
CONECT   11    7   19   22                                                  
CONECT   12    8    9   21                                                  
CONECT   13    8   23   26                                                  
CONECT   14   19   20   28                                                  
CONECT   15   18   22   27                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10   15                                                       
CONECT   19   11   14                                                       
CONECT   20   14   22                                                       
CONECT   21   12   28                                                       
CONECT   22   11   15   20                                                  
CONECT   23   13                                                            
CONECT   24   28                                                            
CONECT   25   28                                                            
CONECT   26    2   13                                                       
CONECT   27    3   15                                                       
CONECT   28   14   21   24   25                                             
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Cloransulam - methyl	ChEBI
DE 565	ChEBI
First Rate	ChEBI
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulfonamido)benzoate	ChEBI
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamido)benzoate	ChEBI
Methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino]benzoate	ChEBI
Methyl 3-chloro-N-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulfonyl)anthranilate	ChEBI
First Ric acid	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulfonamido)benzoic acid	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulphonamido)benzoate	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulphonamido)benzoic acid	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamido)benzoic acid	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonamido)benzoate	Generator
Methyl 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonamido)benzoic acid	Generator
Methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino]benzoic acid	Generator
Methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulphonyl]amino]benzoate	Generator
Methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulphonyl]amino]benzoic acid	Generator
Methyl 3-chloro-N-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulfonyl)anthranilic acid	Generator
Methyl 3-chloro-N-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulphonyl)anthranilate	Generator
Methyl 3-chloro-N-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulphonyl)anthranilic acid	Generator
Cloransulam-methyl, bsi	HMDB
XDE 565	HMDB

Chemical Formula

C₁₅H₁₃ClFN₅O₅S

Average Mass

429.8110 Da

Monoisotopic Mass

429.03100 Da

IUPAC Name

methyl 3-chloro-2-{5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamido}benzoate

Traditional Name

cloransulam

CAS Registry Number

Not Available

SMILES

CCOC1=NC(F)=CC2=NC(=NN12)S(=O)(=O)NC1=C(C=CC=C1Cl)C(=O)OC

InChI Identifier

InChI=1S/C15H13ClFN5O5S/c1-3-27-15-18-10(17)7-11-19-14(20-22(11)15)28(24,25)21-12-8(13(23)26-2)5-4-6-9(12)16/h4-7,21H,3H2,1-2H3

InChI Key

BIKACRYIQSLICJ-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 benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Sulfanilide
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Triazolopyrimidine
Benzoyl
Alkyl aryl ether
Chlorobenzene
Halobenzene
Halopyrimidine
Organosulfonic acid amide
Aryl halide
Pyrimidine
Aryl chloride
Aryl fluoride
Aminosulfonyl compound
Heteroaromatic compound
Vinylogous amide
Methyl ester
1,2,4-triazole
Triazole
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Azole
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Organofluoride
Organopnictogen compound
Organohalogen compound
Organochloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzoate ester (CHEBI:3760 )
Anilide herbicides (C10907 )

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	3.03	ALOGPS
logP	3.16	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.05	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.47 m³·mol⁻¹	ChemAxon
Polarizability	38.66 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0033147

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011150

KNApSAcK ID

Not Available

Chemspider ID

77968

KEGG Compound ID

C10907

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86453

PDB ID

Not Available

ChEBI ID

3760

Good Scents ID

Not Available

References

General References

Lewer P, Finney-Brink KL, Duebelbeis DO: Nature of the residue of [(14)C]Cloransulam-methyl in lactating goats. J Agric Food Chem. 2000 Jun;48(6):2532-46. doi: 10.1021/jf9909611. [PubMed:10888581 ]
Krieger MS, Wynn JL, Yoder RN: Extraction of cloransulam-methyl from soil with subcritical water and supercritical CO2. J Chromatogr A. 2000 Nov 3;897(1-2):405-13. doi: 10.1016/s0021-9673(00)00818-9. [PubMed:11128225 ]
Zhang Z, Li M, Feng M, Zhu K, Han L: Dissipation dynamics and final residues of cloransulam-methyl in soybean and soil. Environ Monit Assess. 2016 Mar;188(3):168. doi: 10.1007/s10661-016-5168-8. Epub 2016 Feb 16. [PubMed:26884355 ]

Showing NP-Card for Cloransulam-methyl (NP0337107)

MOL for NP0337107 (Cloransulam-methyl)

3D MOL for NP0337107 (Cloransulam-methyl)

3D SDF for NP0337107 (Cloransulam-methyl)

3D-SDF for NP0337107 (Cloransulam-methyl)

PDB for NP0337107 (Cloransulam-methyl)

3D PDB for NP0337107 (Cloransulam-methyl)

SMILES for NP0337107 (Cloransulam-methyl)

INCHI for NP0337107 (Cloransulam-methyl)

Structure for NP0337107 (Cloransulam-methyl)

3D Structure for NP0337107 (Cloransulam-methyl)