ContaminantDB: Fusaric Acid

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

Record Information

Version

1.0

Creation Date

2010-05-07 21:39:01 UTC

Update Date

2026-03-31 20:50:42 UTC

Accession Number

CHEM002709

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)

Contaminant Sources

T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Fusarate	Generator
5-Butylpicolinic acid	ChEMBL
5-Butylpicolinate	Generator
5-Butyl-2-pyridinedicarboxylic acid	MeSH
Calcium fusarate	MeSH
Acid, 5-butyl-2-pyridinedicarboxylic	MeSH
Acid, fusaric	MeSH
Fusarate, calcium	MeSH
5 Butyl 2 pyridinedicarboxylic acid	MeSH

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

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

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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002o-5900000000-777718fdc4544fca8492	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-1900000000-e1a5b78275bfaac6fb40	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-1900000000-09b739415eb4cb96a431	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-f0d106fd9bf1d434f23c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2ce774606349e653f3d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-50d68a61b14e617c08f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-35db4e9da777c3b5075e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-cafa852fe8be3fd4f93c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9300000000-cefdd55be23668bf4319	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8a63fef0531b3fc5a15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0900000000-f69fac621a74bd89a815	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-4900000000-1c37bf3cd6b4fc7d114e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-0417a01f6b57ca90489f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9800000000-51ee66f3ec8d1b448190	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-3a36838d6d1d894af158	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-e9e4d0ba83478e578c42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0900000000-7b0f82ed39313b957e89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9300000000-3a765909f3e0e86772e5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000l-9700000000-405767e6fd1d1ffcd255	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	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)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0252556

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002040

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3324

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C10146

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Fusaric Acid (CHEM002709)

Structure for CHEM002709: Fusaric Acid