ContaminantDB: Bovinocidin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2010-05-03 15:06:51 UTC

Update Date

2026-04-04 02:23:06 UTC

Accession Number

CHEM002693

Identification

Common Name

Bovinocidin

Class

Small Molecule

Description

Bovinocidin is isolated from Aspergillus sp. and moulds contaminating food Bovinocidin belongs to the family of Beta Amino Acids and Derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Contaminant Sources

FooDB Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Nitropropionic acid	ChEBI
beta-Nitropropanoic acid	ChEBI
beta-Nitropropionic acid	ChEBI
3-Nitropropanoate	Kegg
3-Nitropropionate	Generator
b-Nitropropanoate	Generator
b-Nitropropanoic acid	Generator
beta-Nitropropanoate	Generator
Β-nitropropanoate	Generator
Β-nitropropanoic acid	Generator
b-Nitropropionate	Generator
b-Nitropropionic acid	Generator
beta-Nitropropionate	Generator
Β-nitropropionate	Generator
Β-nitropropionic acid	Generator
3-Nitropropanoic acid	Generator
3-nitro-1-Propionate	HMDB
3-nitro-Propanoic acid	HMDB
3-nitro-Propionic acid	HMDB
3-Nitropropionic acid, 8ci	HMDB
3-NP acid	HMDB, MeSH
3-NPA	HMDB
504-88-1 (FREE acid)	HMDB
beta -Nitropropionic acid	HMDB
BNP	HMDB
Hiptagenic acid	HMDB
Nitropropionic acid, beta	HMDB
NSC 64266	HMDB
Propanoic acid, 3-nitro- (9ci)	HMDB
Propionate 3-nitronate	MeSH, HMDB
Bovinocidin	ChEBI

Chemical Formula

C₃H₅NO₄

Average Molecular Mass

119.076 g/mol

Monoisotopic Mass

119.022 g/mol

CAS Registry Number

504-88-1

IUPAC Name

3-nitropropanoic acid

Traditional Name

β-nitropropionic acid

SMILES

OC(=O)CCN(=O)=O

InChI Identifier

InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)

InChI Key

WBLZUCOIBUDNBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon.

Kingdom

Organic compounds

Super Class

Organic 1,3-dipolar compounds

Class

Allyl-type 1,3-dipolar organic compounds

Sub Class

Organic nitro compounds

Direct Parent

C-nitro compounds

Alternative Parents

Substituents

C-nitro compound
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
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
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C-nitro compound (CHEBI:16348 )

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	64 - 65°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	13.6 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	-0.27	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	23.37 m³·mol⁻¹	ChemAxon
Polarizability	9.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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	splash10-00di-9100000000-c84646547cc314df783e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9500000000-ff7957d32f819292d644	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-2900000000-b06f8e6c082d20a54d6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9100000000-08c8f64733feed89812a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bti-9000000000-ef962de7ab2944fcaa9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-7900000000-d8fc1c7d184d25bb9c5b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uki-9500000000-9efcc70c860c5ed1033a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9000000000-28a52986668d447dc00b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9700000000-7764bae0c8f7785cb8ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-39537a3c0fd0f755292a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9000000000-94855126f2f5e14340d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00r2-9700000000-171d4328fbe5a0ba1cb4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-17277526de0706b5782c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-a0441e6336543cb88423	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	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	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	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (6)

Mechanism of Toxicity

3-Nitropropionic acid is a suicide inhibitor of succinate dehydrogenase, an enzyme required for the activity of the tricarboxylic acid (TCA) cycle as well as mitochondrial respiratory complex II of the electron transport chain. It forms a covalent adduct with the side chain of Arg297, inactivating the succinate dehydrogenase. This affects neurons by leading to NMDA-receptor activation, excessive calcium influx, and formation of reactive oxygen species, eventually causing neuronal cell death. (1, 2)

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

3-Nitropropionic acid is a neurotoxin produced by certain plants and fungi, such as those of the genus Astragalus, Coronilla, Lotus, Hippocrepis, Scorpiurus, and Securigera. It produces symptoms similar to that of Huntington disease and this thus often used to produced animal models for the study of the disease. (1, 2, 4)

Minimum Risk Level

Not Available

Health Effects

3-Nitropropionic acid causes neurodegeneration, particularity of the striatum, though also in the hippocampus and thalamus. (1, 5)

Symptoms

3-Nitropropionic acid causes symptoms similar to that of Huntington disease: motor and cognitive dysfunction that includes convulsions, dystonia, and hypokinesia. (1, 3, 5)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034259

FooDB ID

FDB012579

Phenol Explorer ID