Harzianic acid

Modify Date: 2024-01-14 13:43:00

Harzianic acid Structure
Harzianic acid structure
Common Name Harzianic acid
CAS Number 157148-06-6 Molecular Weight 365.42100
Density 1.233g/cm3 Boiling Point 539.8ºC at 760mmHg
Molecular Formula C19H27NO6 Melting Point N/A
MSDS N/A Flash Point 280.3ºC

 Use of Harzianic acid


Harzianic acid, a tetramic acid derivative, with activity of antimicrobial, antibiofilm formation and biofilm disaggregation. Harzianic acid interferes with biofilm formation by limiting bacterial iron availability. Harzianic acid is also a selective inhibitor of Acetohydroxyacid synthase (AHAS), the first enzyme in the branched-chain amino acid biosynthetic pathway. Harzianic acid can used for herbicide and fungicide[1][2].

 Names

Name 2-hydroxy-2-[[(4E)-4-[(2E,4E)-1-hydroxyocta-2,4-dienylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl]-3-methylbutanoic acid
Synonym More Synonyms

 Harzianic acid Biological Activity

Description Harzianic acid, a tetramic acid derivative, with activity of antimicrobial, antibiofilm formation and biofilm disaggregation. Harzianic acid interferes with biofilm formation by limiting bacterial iron availability. Harzianic acid is also a selective inhibitor of Acetohydroxyacid synthase (AHAS), the first enzyme in the branched-chain amino acid biosynthetic pathway. Harzianic acid can used for herbicide and fungicide[1][2].
Related Catalog
Target

Acetohydroxyacid synthase (AHAS)[2]

In Vitro Harzianic acid 对 MRSP 和 MSSP 表现出较强的抑菌活性,MIC 值分别为 32 μg/mL 和 16 μg/mL [1]。 Harzianic acid (8-128 μg/mL) 对 HaCaT 细胞毒性较低[1]。 Harzianic acid 作为一种竞争性抑制剂抑制真菌 ThAHAS, Ki 为 6.65 μM[2]。 Harzianic acid (0.1-100 μg/mL) 对病原真菌的生长有抑制作用[2]。
References

[1]. De Filippis A, et al. Antimicrobial activity of harzianic acid against Staphylococcus pseudintermedius. Nat Prod Res. 2021 Dec;35(23):5440-5445.  

[2]. Xie L, et al. Harzianic Acid from Trichoderma afroharzianum Is a Natural Product Inhibitor of Acetohydroxyacid Synthase. J Am Chem Soc. 2021 Jun 16:10.1021/jacs.1c03988.  

 Chemical & Physical Properties

Density 1.233g/cm3
Boiling Point 539.8ºC at 760mmHg
Molecular Formula C19H27NO6
Molecular Weight 365.42100
Flash Point 280.3ºC
Exact Mass 365.18400
PSA 115.14000
LogP 1.92040
Vapour Pressure 6.63E-14mmHg at 25°C
Index of Refraction 1.561

 Synonyms

Harzianic acid
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