T3DB: Fusaric Acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2010-05-07 21:39:01 UTC

Update Date

2014-12-24 20:26:29 UTC

Accession Number

T3D3741

Identification

Common Name

Fusaric Acid

Class

Small Molecule

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. (6, 1)

Compound Type

Ester
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
5-Butyl-2-pyridinecarboxylic acid
5-Butyl-2-pyridinedicarboxylic acid
5-Butyl-pyridine-2-carboxylic acid
5-Butyl-pyridine-2-carboxylic acid (fusaric acid)
5-Butylpicolinic acid
5-Butylpyridine-2-carboxylic acid
5-Butylpyridine-3-carboxylic acid
5-n-Butylpyridine-2-carboxylic acid
Calcium fusarate
Fusarate
fusaric acid
Fusaric acid
Fusarinic acid
Picolinic acid, 5-butyl- (8CI)

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Mass

179.216 g/mol

Monoisotopic Mass

179.095 g/mol

CAS Registry Number

536-69-6

IUPAC Name

5-butylpyridine-2-carboxylic acid

Traditional Name

fusaric acid

SMILES

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

InChI Identifier

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)

InChI Key

InChIKey=DGMPVYSXXIOGJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

5-alkyl-2-carboxypyrimidines

Alternative Parents

Substituents

5-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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:5199 )
aromatic carboxylic acid (CHEBI:5199 )
Piperidine alkaloids (C10146 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.73 g/L	ALOGPS
logP	1.99	ALOGPS
logP	1.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.13	ChemAxon
pKa (Strongest Basic)	5.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.63 m³·mol⁻¹	ChemAxon
Polarizability	19.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002o-5900000000-777718fdc4544fca8492	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-1900000000-e1a5b78275bfaac6fb40	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-1900000000-09b739415eb4cb96a431	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-f0d106fd9bf1d434f23c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2ce774606349e653f3d9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-50d68a61b14e617c08f1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-35db4e9da777c3b5075e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-cafa852fe8be3fd4f93c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9300000000-cefdd55be23668bf4319	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8a63fef0531b3fc5a15b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0900000000-f69fac621a74bd89a815	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-4900000000-1c37bf3cd6b4fc7d114e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-0417a01f6b57ca90489f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9800000000-51ee66f3ec8d1b448190	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-3a36838d6d1d894af158	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-e9e4d0ba83478e578c42	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0900000000-7b0f82ed39313b957e89	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9300000000-3a765909f3e0e86772e5	2021-10-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000l-9700000000-405767e6fd1d1ffcd255	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

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. (1, 2, 3, 4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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 can be found in contaminated corn and cereal grains including barley, wheat, millets and sorghum. (6, 1)

Minimum Risk Level

Not Available

Health Effects

Fusaric acid can contribute to mycotic keratitis infections. It also has developmental and neurological effects. (2, 4)

Symptoms

Fusaric acid can cause vomiting, hypotension, and alterations in behavioral and locomotive activity. (1, 3, 4)

Treatment

Natamycin ophthalmic suspension is the drug of choice for filamentous fungal infections such as mycotic keratitis. (7)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Fusaric_acid

References

Synthesis Reference

Not Available

MSDS

T3D3741.pdf

General References

Wang H, Ng TB: Pharmacological activities of fusaric acid (5-butylpicolinic acid). Life Sci. 1999;65(9):849-56. [10465344 ]
Naiker S, Odhav B: Mycotic keratitis: profile of Fusarium species and their mycotoxins. Mycoses. 2004 Feb;47(1-2):50-6. [14998400 ]
Porter JK, Bacon CW, Wray EM, Hagler WM Jr: Fusaric acid in Fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats. Nat Toxins. 1995;3(2):91-100. [7542129 ]
Reddy RV, Larson CA, Brimer GE, Frappier BL, Reddy CS: Developmental toxic effects of fusaric acid in CD1 mice. Bull Environ Contam Toxicol. 1996 Sep;57(3):354-60. [8672059 ]
Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Wikipedia. Fusaric Acid. Last Updated 12 March 2010. [Link]
Wikipedia. Fungal Keratitis. Last Updated 26 March 2010. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. 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

References

Wang H, Ng TB: Pharmacological activities of fusaric acid (5-butylpicolinic acid). Life Sci. 1999;65(9):849-56. [10465344 ]
Naiker S, Odhav B: Mycotic keratitis: profile of Fusarium species and their mycotoxins. Mycoses. 2004 Feb;47(1-2):50-6. [14998400 ]
Porter JK, Bacon CW, Wray EM, Hagler WM Jr: Fusaric acid in Fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats. Nat Toxins. 1995;3(2):91-100. [7542129 ]
Reddy RV, Larson CA, Brimer GE, Frappier BL, Reddy CS: Developmental toxic effects of fusaric acid in CD1 mice. Bull Environ Contam Toxicol. 1996 Sep;57(3):354-60. [8672059 ]

Target Details

2. 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

References

Wang H, Ng TB: Pharmacological activities of fusaric acid (5-butylpicolinic acid). Life Sci. 1999;65(9):849-56. [10465344 ]
Naiker S, Odhav B: Mycotic keratitis: profile of Fusarium species and their mycotoxins. Mycoses. 2004 Feb;47(1-2):50-6. [14998400 ]
Porter JK, Bacon CW, Wray EM, Hagler WM Jr: Fusaric acid in Fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats. Nat Toxins. 1995;3(2):91-100. [7542129 ]
Reddy RV, Larson CA, Brimer GE, Frappier BL, Reddy CS: Developmental toxic effects of fusaric acid in CD1 mice. Bull Environ Contam Toxicol. 1996 Sep;57(3):354-60. [8672059 ]

Target Details

3. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
IC50	149 uM	Not Available	BindingDB 50000439

References

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 ]

Fusaric Acid (T3D3741)

Structure for T3D3741: Fusaric Acid

Targets

References

References

Binding/Activity Constants

References