Fusaric Acid

Basic Info

Common NameFusaric Acid(F04986)
2D Structure
Description

Fusaric acid is a mycotoxin found in various Fusarium species such as Fusarium moniliforme. It has been proposed for a various therapeutic applications but is primarily used as a research tool. Fusaric acid is moderately toxic and can be found in contaminated corn and cereal grains including barley, wheat, millets and sorghum. (L1963, A3020)

FRCD IDF04986
CAS Number536-69-6
PubChem CID3442
FormulaC10H13NO2
IUPAC Name

5-butylpyridine-2-carboxylic acid

InChI Key

DGMPVYSXXIOGJY-UHFFFAOYSA-N

InChI

InChI=1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13)

Canonical SMILES

CCCCC1=CN=C(C=C1)C(=O)O

Isomeric SMILES

CCCCC1=CN=C(C=C1)C(=O)O

WikipediaFusaric Acid
Synonyms
        
            fusaric acid
        
            5-Butylpicolinic acid
        
            536-69-6
        
            5-Butylpyridine-2-carboxylic acid
        
            Fusarinic acid
        
            2-Pyridinecarboxylic acid, 5-butyl-
        
            5-Butyl-2-pyridinecarboxylic acid
        
            Picolinic acid, 5-butyl-
        
            5-n-Butylpyridine-2-carboxylic acid
        
            UNII-JWJ963070N
Classifies
                

                  
                    Fungal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassPyridines and derivatives
SubclassPyridinecarboxylic acids and derivatives
Intermediate Tree NodesPyridinecarboxylic acids - Pyridine-2-carboxylic acids
Direct Parent5-alkyl-2-carboxypyrimidines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents5-alkyl-2-carboxypyrimidine - Heteroaromatic compound - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 5-alkyl-2-carboxypyrimidines. These are pyrimidine-2-carboxylic acids that carry an alkyl group at the 5-position of the pyridine ring.

Properties

Property NameProperty Value
Molecular Weight179.219
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity170
Monoisotopic Mass179.095
Exact Mass179.095
XLogP2.6
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9547
Human Intestinal AbsorptionHIA+0.9951
Caco-2 PermeabilityCaco2+0.7789
P-glycoprotein SubstrateNon-substrate0.6758
P-glycoprotein InhibitorNon-inhibitor0.9881
Non-inhibitor0.9892
Renal Organic Cation TransporterNon-inhibitor0.8904
Distribution
Subcellular localizationPlasma membrane0.4770
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7402
CYP450 2D6 SubstrateNon-substrate0.8377
CYP450 3A4 SubstrateNon-substrate0.7813
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9574
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.9298
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9655
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9546
Non-inhibitor0.9810
AMES ToxicityNon AMES toxic0.9723
CarcinogensNon-carcinogens0.9219
Fish ToxicityHigh FHMT0.5308
Tetrahymena Pyriformis ToxicityHigh TPT0.8681
Honey Bee ToxicityLow HBT0.6303
BiodegradationReady biodegradable0.7581
Acute Oral ToxicityII0.7473
Carcinogenicity (Three-class)Non-required0.7024
Model Value Unit
Absorption
Aqueous solubility-2.0255LogS
Caco-2 Permeability1.4973LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5409LD50, mol/kg
Fish Toxicity2.1783pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5387pIGC50, ug/L

References

TitleJournalDatePubmed ID
Analysis of the global regulator Lae1 uncovers a connection between Lae1 and the histone acetyltransferase HAT1 in Fusarium fujikuroi.Appl Microbiol Biotechnol2018 Jan29080998
Comparative genomics of geographically distant Fusarium fujikuroi isolatesrevealed two distinct pathotypes correlating with secondary metabolite profiles.PLoS Pathog2017 Oct 2629073267
Antifungal Activity and Action Mode of Cuminic Acid from the Seeds of Cuminum cyminum L. against Fusarium oxysporum f. sp. Niveum (FON) Causing Fusarium Wilt on Watermelon.Molecules2017 Nov 3029189726
Detoxification of Fusaric Acid by the Soil Microbe Mucor rouxii.J Agric Food Chem2017 Jun 2128538103
Emerging Mycotoxins: Beyond Traditionally Determined Food Contaminants.J Agric Food Chem2017 Aug 2327599910
Fusarium Species and Their Associated Mycotoxins.Methods Mol Biol201727924531
Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2).Plant Cell Rep2016 Feb26518425
Mycotoxigenic Potentials of Fusarium Species in Various Culture Matrices Revealed by Mycotoxin Profiling.Toxins (Basel)2016 Dec 2628035973
Isolation and Structure Elucidation of Fujikurins A-D: Products of the PKS19 Gene Cluster in Fusarium fujikuroi.J Nat Prod2015 Aug 2826192387
Fungal and bacterial metabolites associated with natural contamination of locally processed rice (Oryza sativa L.) in Nigeria.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525767914
Role of the European corn borer (Ostrinia nubilalis) on contamination of maize with 13 Fusarium mycotoxins.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525266165
Screening survey of co-production of fusaric acid, fusarin C, and fumonisins B₁, B₂ and B₃ by Fusarium strains grown in maize grains.Mycotoxin Res2014 Nov25270005
The effects of different yeast extracts on secondary metabolite production inFusarium.Int J Food Microbiol2014 Jan 1724291181
Determination of fusaric acid in maize using molecularly imprinted SPE clean-up.J Sep Sci2014 Feb24227222
Fusarium verticillioides SGE1 is required for full virulence and regulates expression of protein effector and secondary metabolite biosynthetic genes.Mol Plant Microbe Interact2014 Aug24742071
Masked mycotoxins: a review.Mol Nutr Food Res2013 Jan23047235
Contamination of bananas with beauvericin and fusaric acid produced by Fusarium oxysporum f. sp. cubense.PLoS One201323922960
Mycotoxins in corn and wheat silage in Israel.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201323789893
Ultrahigh-performance liquid chromatographic-tandem mass spectrometric multimycotoxin method for quantitating 26 mycotoxins in maize silage.J Agric Food Chem2011 Sep 2821888373
Single-kernel analysis of fumonisins and other fungal metabolites in maize from South African subsistence farmers.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011 Dec22023397

Targets

Target Details

Tyrosine 3-monooxygenase

General Function:
Tyrosine 3-monooxygenase activity
Specific Function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular Weight:
58599.545 Da
Mechanism of Action:
Fusaric acid affects neurotransmitter levels by acting as a partial inhibitor on tyrosine-hydroxylase and an inhibitor on dopamine-beta-hydroxylase. This has been shown to cause elevated serotonin, 5-hydroxyindoleacetic acid, tyrosine, and dopamine levels in the brain, as well as decreased norepinephrine levels. These changes in neurotransmitter levels may be responsible for effects such as hypotension, altered behavior and locomotive activity, neurological disorders, and developmental problems.
References
  1. Wang H, Ng TB: Pharmacological activities of fusaric acid (5-butylpicolinic acid). Life Sci. 1999;65(9):849-56. [10465344 ]
Target Details

Transmembrane prolyl 4-hydroxylase

General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, 2-oxoglutarate as one donor, and incorporation of one atom each of oxygen into both donors
Specific Function:
Catalyzes the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates HIF1A at 'Pro-402' and 'Pro-564'. May function as a cellular oxygen sensor and, under normoxic conditions, may target HIF through the hydroxylation for proteasomal degradation via the von Hippel-Lindau ubiquitination complex.
Gene Name:
P4HTM
Uniprot ID:
Q9NXG6
Molecular Weight:
56660.535 Da
References
  1. Tucker H, Thomas DF: Novel inhibitors of prolyl 4-hydroxylase. 2. 5-Amide substituted pyridine-2-carboxylic acids. J Med Chem. 1992 Mar 6;35(5):804-7. [1312599 ]
Target Details

Dopamine beta-hydroxylase

General Function:
L-ascorbic acid binding
Specific Function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular Weight:
69064.45 Da
Mechanism of Action:
Fusaric acid affects neurotransmitter levels by acting as a partial inhibitor on tyrosine-hydroxylase and an inhibitor on dopamine-beta-hydroxylase. This has been shown to cause elevated serotonin, 5-hydroxyindoleacetic acid, tyrosine, and dopamine levels in the brain, as well as decreased norepinephrine levels. These changes in neurotransmitter levels may be responsible for effects such as hypotension, altered behavior and locomotive activity, neurological disorders, and developmental problems.
References
  1. Wang H, Ng TB: Pharmacological activities of fusaric acid (5-butylpicolinic acid). Life Sci. 1999;65(9):849-56. [10465344 ]