Np mrd loader

Showing NP-Card for Fusaric acid (NP0051127)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 22:32:54 UTC
Updated at2025-10-07 01:01:25 UTC
NP-MRD IDNP0051127
Natural Product DOIhttps://doi.org/10.57994/4374
Secondary Accession NumbersNone
Natural Product Identification
Common NameFusaric acid
DescriptionFusaric Acid, also known as fusarate, 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. Fusaric Acid is a very strong basic compound (based on its pKa). Fusaric Acid is a potentially toxic compound. Natamycin ophthalmic suspension is the drug of choice for filamentous fungal infections such as mycotic keratitis. This has been shown to cause elevated serotonin, 5-hydroxyindoleacetic acid, tyrosine, and dopamine levels in the brain, as well as decreased norepinephrine levels. It has been proposed for a various therapeutic applications but is primarily used as a research tool. It also has developmental and neurological effects. These changes in neurotransmitter levels may be responsible for effects such as hypotension, altered behavior and locomotive activity, neurological disorders, and developmental problems. Fusaric acid is moderately toxic and can be found in contaminated corn and cereal grains including barley, wheat, millets and sorghum. Fusaric acid is a mycotoxin found in various Fusarium species such as Fusarium moniliforme. Fusaric acid affects neurotransmitter levels by acting as a partial inhibitor on tyrosine-hydroxylase and an inhibitor on dopamine-beta-hydroxylase. Fusaric acid can contribute to mycotic keratitis infections. Fusaric acid is found in Fusarium nygamai, Fusarium oxysporum, Fusarium solani and Fusarium verticillioides. Fusaric acid was first documented in 2025 (PMID: 40893048). Fusaric acid can cause vomiting, hypotension, and alterations in behavioral and locomotive activity.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051127 (Fusaric acid)


  Mrv0541 02241212472D          

 13 13  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0051127 (Fusaric acid)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    2.7758    1.6082    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    0.6489    1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2405   -0.7726    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -1.0748   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0197   -0.7513   -0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108   -1.6613   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -1.3217    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877   -0.0768   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835    0.3250   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9354   -0.4968    0.2111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5188    1.5848   -0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    0.8115   -0.7388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4529    0.4958   -0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476    1.7892    0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7400    1.2134   -0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    2.5977    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923    0.9605    1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253    0.7283    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8788   -1.4236    1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -1.0638    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863   -0.6101   -1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5308   -2.1775   -0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140   -2.6451    0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -2.0488    0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767    2.0851    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1945    1.2760   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 13  2  0
 13 12  1  0
 12  8  2  0
  8  7  1  0
  7  6  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  6  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
 13 26  1  0
  7 24  1  0
  6 23  1  0
 11 25  1  0
M  END
Download

3D SDF for NP0051127 (Fusaric acid)


  Mrv0541 02241212472D          

 13 13  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051127

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H13NO2

> <MOLECULAR_WEIGHT>
179.2157

> <EXACT_MASS>
179.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.6665813917763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-butylpyridine-2-carboxylic acid

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.096355931952567

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1307683233465315

> <JCHEM_PKA_STRONGEST_BASIC>
5.857842461320446

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
49.62950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fusaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0051127 (Fusaric acid)

Download
PDB for NP0051127 (Fusaric acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0051127 (Fusaric acid)
Download
SMILES for NP0051127 (Fusaric acid)
CCCCC1=CN=C(C=C1)C(O)=O
Download
INCHI for NP0051127 (Fusaric acid)
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)
Download
View in JSmol
Synonyms
ValueSource
FusarateGenerator
5-Butylpicolinic acidChEMBL
5-ButylpicolinateGenerator
5-Butyl-2-pyridinedicarboxylic acidMeSH
Calcium fusarateMeSH
Acid, 5-butyl-2-pyridinedicarboxylicMeSH
Acid, fusaricMeSH
Fusarate, calciumMeSH
5 Butyl 2 pyridinedicarboxylic acidMeSH
Chemical FormulaC10H13NO2
Average Mass179.2157 Da
Monoisotopic Mass179.09463 Da
IUPAC Name5-butylpyridine-2-carboxylic acid
Traditional Namefusaric acid
CAS Registry NumberNot Available
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 KeyDGMPVYSXXIOGJY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)[email protected]Universidade de São PauloVitor de Souza Mazucato2025-10-06View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium guttiforme
      Not Available
Fusarium nygamaiLOTUS Database
Fusarium oxysporumFungi
Fusarium solaniLOTUS Database
Fusarium verticillioidesLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassPyridinecarboxylic acids and derivatives  
Direct Parent5-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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.99ALOGPS
logP1.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.13ChemAxon
pKa (Strongest Basic)5.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.63 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002040  
Chemspider IDNot Available
KEGG Compound IDC10146  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3442  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. DOI: 10.1002/cbdv.202501135
  2. PMID: 40893048