Thaxtomin A - ≥98% , CAS No.122380-18-1

CAS: 122380-18-1 Cat. No.: T276425 Molecular Weight: 438.43 PubChem CID: 180098

GRADE & PURITY ≥98%

Synonyms

Thaztomin A | (3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione | Thaxtomin A | SCHEMBL12381685 | Thaxtomine A | HY-124212 | HB4107 | 2,5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

Thaztomin A | (3R, 6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1, 4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2, 5-dione | Thaxtomin A | SCHEMBL12381685 | Thaxtomine A | HY-124212 | HB4107 | 2, 5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Phytotoxin and potent necrotic agent. Cellulose synthesis inhibitor. Bacterial NOS metabolite. Inhibits cellulose synthesis in expanding plant tissues. Herbicidal effects in vivo.Cellulose synthesis inhibition by thaxtomin A, indicates plant-pathogen inte

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504757707
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757707
• Canonical Smiles: CN1C(C(=O)N(C(C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]
• IUPAC Name: (3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione
• InChIKey: QRDNJYNIEGRRKV-PGRDOPGGSA-N
• INCHI: 1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22+/m0/s1
• Isomeric SMILES: CN1[C@H](C(=O)N([C@](C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]
• PubChem CID: 180098
• Molecular Weight: 438.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: 3-alkylindoles 2,5-dioxopiperazines Nitroaromatic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids N-methylpiperazines Substituted pyrroles Benzene and substituted derivatives Tertiary carboxylic acid amides Heteroaromatic compounds Lactams Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Alkanolamines Azacyclic compounds Organic zwitterions Organopnictogen compounds Organic oxides Carbonyl compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - 3-alkylindole - Indole - Indole or derivatives - Nitroaromatic compound - Dioxopiperazine - 2,5-dioxopiperazine - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - N-alkylpiperazine - N-methylpiperazine - Phenol - Monocyclic benzene moiety - 1,4-diazinane - Benzenoid - Piperazine - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Tertiary carboxylic acid amide - Carboxamide group - Lactam - C-nitro compound - Organic nitro compound - Organoheterocyclic compound - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic oxoazanium - Alkanolamine - Azacycle - Organic zwitterion - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: Not available

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)

Echinochloa crus-galli (3685 Activities)

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Arabidopsis thaliana (307 Activities)

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Helianthus annuus (57 Activities)

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Avena fatua (609 Activities)

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Abutilon theophrasti (831 Activities)

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Ipomoea hederacea (88 Activities)

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Lemna minor (73 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol and in DMSO
• Sensitivity: Light sensitive
• Molecular Weight: 438.400 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 438.154 Da
• Monoisotopic Mass: 438.154 Da
• Topological Polar Surface Area: 143.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 759.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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