GRADE & PURITY ≥90%

Synonyms

CHEBI:51015 | 1o9e | fuscicoccin A | FSC | [(2S)-2-[(1E,3R,4S,8R,9R,10R,11S,14S)-8-[(2S,3R,4S,5R,6R)-4-acetyloxy-3,5-dihydroxy-6-(2-methylbut-3-en-2-yloxymethyl)oxan-2-yl]oxy-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-tricyclo[9.3.0.03,7]tetradeca-1

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Source：Isolated from Fusicoccum amygdali.

application：

Fusicoccin (Fusicoccin A), a diterpene glucoside phytotoxin, is used to study 14-3-3-dependent processes such as the activation of H+-ATPase in plants and other client proteins with mode III binding motifs. Fusicoccin is an inducer of a catalase inhibitor that leads to oxidative damage in plants.

Specifications

Synonyms

CHEBI:51015 | 1o9e | fuscicoccin A | FSC | [(2S)-2-[(1E, 3R, 4S, 8R, 9R, 10R, 11S, 14S)-8-[(2S, 3R, 4S, 5R, 6R)-4-acetyloxy-3, 5-dihydroxy-6-(2-methylbut-3-en-2-yloxymethyl)oxan-2-yl]oxy-4, 9-dihydroxy-14-(methoxymethyl)-3, 10-dimethyl-6-tricyclo[9.3.0.03, 7]tetradeca-1

Specifications & Purity

≥90%

Biochemical and Physiological Mechanisms

H + -ATPase activator. NF-κB activator. 14-3-3 protein binder. Induces H + extrusion from plant cells. Stimulates cytochrome c release from mitochondria. Reduces cellular H 2 O 2 scavenging capacity. Induces membrane hyperpolarization.

Storage

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

≥90%

Names and Identifiers

• Canonical Smiles: CC1C2CCC(C2=CC3(C(CC(=C3C(C1O)OC4C(C(C(C(O4)COC(C)(C)C=C)O)OC(=O)C)O)C(C)COC(=O)C)O)C)COC
• IUPAC Name: [(2S)-2-[(1E,3R,4S,8R,9R,10R,11S,14S)-8-[(2S,3R,4S,5R,6R)-4-acetyloxy-3,5-dihydroxy-6-(2-methylbut-3-en-2-yloxymethyl)oxan-2-yl]oxy-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-tricyclo[9.3.0.03,7]tetradeca-1,6-dienyl]propyl] acetate
• InChIKey: KXTYBXCEQOANSX-WYKQKOHHSA-N
• INCHI: 1S/C36H56O12/c1-10-35(6,7)45-17-26-30(41)33(46-21(5)38)31(42)34(47-26)48-32-28-24(18(2)15-44-20(4)37)13-27(39)36(28,8)14-25-22(16-43-9)11-12-23(25)19(3)29(32)40/h10,14,18-19,22-23,26-27,29-34,39-42H,1,11-13,15-17H2,2-9H3/b25-14-/t18-,19-,22-,23+,26-,27+,29-,30-,31-,32-,33+,34-,36+/m1/s1
• Isomeric SMILES: C[C@@H]1[C@@H]\2CC[C@@H](/C2=C/[C@]3([C@H](CC(=C3[C@H]([C@@H]1O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(C)(C)C=C)O)OC(=O)C)O)[C@H](C)COC(=O)C)O)C)COC
• Molecular Weight: 680.82
• Reaxy-Rn: 34887837
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=34887837&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpene glycosides
• Alternative Parents: Fusicoccane diterpenoids O-glycosyl compounds Oxanes Monosaccharides Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters Oxacyclic compounds Dialkyl ethers Acetals Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Diterpene glycoside - Diterpenoid - Fusicoccane diterpenoid - Glycosyl compound - O-glycosyl compound - Dicarboxylic acid or derivatives - Monosaccharide - Oxane - Carboxylic acid ester - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Ether - Dialkyl ether - Acetal - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
• External Descriptors: acetate ester

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(Human)

YWHAZ Tchem 14-3-3 protein zeta/delta (1 Activities)

Discover Target: YWHAZ

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in chloroform and ethanol. Slightly soluble in ethyl acetate and ethyl ether. Sparingly soluble in acetone.
• Molecular Weight: 680.800 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 14
• Exact Mass: 680.377 Da
• Monoisotopic Mass: 680.377 Da
• Topological Polar Surface Area: 170.000 Ų
• Heavy Atom Count: 48
• Formal Charge: 0
• Complexity: 1240.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 13
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Jinye Huang, Xuan Xuan, Dongmei Xu, Yuezhong Wen.  (2024)  Dual-Mediated Roles of H+-ATPase in Alleviating the Phytotoxicity of Imazethapyr to Nontarget Wheat.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:39183467] [10.1021/acs.jafc.4c06062]