Acibenzolar-S-methyl - analytical standard,Moligand™ , CAS No.135158-54-2

CAS: 135158-54-2 Cat. No.: A114427 Molecular Weight: 210.28 EC Number: 420-050-0

GRADE & PURITY Analytical standard, Moligand™

Synonyms

MFCD00016396 | UNII-BCW6119347 | DTXSID1032519 | CHEBI:73178 | Ethanone,1-(4-bromophenyl)-2-phenyl- | J-006653 | CGA 245704 | Isoamyl 2-methylpropanoate | benzo-(1,2,3)-thiadiazole-7-carbothioic acid S-methyl ester | benzo(1,2,3)-thiadiazole-7-carbothioic

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

Acibenzolar-S-methyl (ASM) is a plant resistance inducer that mimics pathogen-host interactions and leads to systemic acquired resistance in plants. Acibenzolar-S-methyl helps reduce the use of pesticides and can be used in research to prevent plant diseases.

Specifications

Synonyms

MFCD00016396 | UNII-BCW6119347 | DTXSID1032519 | CHEBI:73178 | Ethanone, 1-(4-bromophenyl)-2-phenyl- | J-006653 | CGA 245704 | Isoamyl 2-methylpropanoate | benzo-(1, 2, 3)-thiadiazole-7-carbothioic acid S-methyl ester | benzo(1, 2, 3)-thiadiazole-7-carbothioic

Specifications & Purity

analytical standard, Moligand™

Storage

Protected from light, Room temperature

Shipped In

Normal

Grade

Analytical standard, Moligand™

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CSC(=O)C1=C2C(=CC=C1)N=NS2
• IUPAC Name: S-methyl 1,2,3-benzothiadiazole-7-carbothioate
• InChIKey: UELITFHSCLAHKR-UHFFFAOYSA-N
• INCHI: 1S/C8H6N2OS2/c1-12-8(11)5-3-2-4-6-7(5)13-10-9-6/h2-4H,1H3
• Isomeric SMILES: CSC(=O)C1=C2C(=CC=C1)N=NS2
• WGK Germany: 3
• Molecular Weight: 210.28
• Reaxy-Rn: 8055445
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8055445&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzothiadiazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzothiadiazoles
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzothiadiazoles
• Alternative Parents: Thiobenzoic acids and derivatives Thiadiazoles Heteroaromatic compounds Thioesters Carbothioic S-esters Sulfenyl compounds Carboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1,2,3-benzothiadiazole - Thiobenzoic acid or derivatives - Benzenoid - Azole - Thiadiazole - Heteroaromatic compound - Carbothioic s-ester - Thiocarboxylic acid ester - Azacycle - Sulfenyl compound - Thiocarboxylic acid or derivatives - Carboxylic acid derivative - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzothiadiazoles. These are heterocyclic aromatic compounds containing a benzene ring fused to a thiadiazole ring. Thiadiazole is a five-membered aromatic heterocycle made up of one sulfur atom and two nitrogen atoms.
• External Descriptors: thioester - benzothiadiazole

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Nicotiana tabacum (382 Activities)

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Oryza sativa (2923 Activities)

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Glycine max (342 Activities)

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Triticum aestivum (1582 Activities)

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Phytophthora capsici (336 Activities)

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Botrytis cinerea (4183 Activities)

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Tobacco mosaic virus (2972 Activities)

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Ascochyta rabiei (17 Activities)

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Rhizoctonia solani (2251 Activities)

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Solanum lycopersicum (493 Activities)

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Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

Discover Target: Nr1i2

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Cyclamen persicum (5 Activities)

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Puccinia triticina (278 Activities)

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Solanum melongena (11 Activities)

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Cucurbita pepo (17 Activities)

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Fusarium oxysporum f. sp. cyclaminis (5 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Molecular Weight: 210.300 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 209.992 Da
• Monoisotopic Mass: 209.992 Da
• Topological Polar Surface Area: 96.400 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 212.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Huanpeng Li, Jiaojiao Wu, Xiaofeng Shang, Miaomiao Geng, Jing Gao, Shuqing Zhao, Xiumei Yu, Daqun Liu, Zhensheng Kang, Xiaojie Wang, Xiaodong Wang.  (2020)  WRKY Transcription Factors Shared by BTH-Induced Resistance and NPR1-Mediated Acquired Resistance Improve Broad-Spectrum Disease Resistance in Wheat.  MOLECULAR PLANT-MICROBE INTERACTIONS,      [PMID:31821091] [10.1094/MPMI-09-19-0257-R]