T3DB: Bovinocidin

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

Targets (4)

Record Information

Version

2.0

Creation Date

2010-05-03 15:06:51 UTC

Update Date

2014-12-24 20:26:27 UTC

Accession Number

T3D3724

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.

Compound Type

Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
3-Nitro-1-propionate
3-Nitro-Propanoic acid
3-Nitro-Propionic acid
3-Nitropropanoate
3-Nitropropionate
3-Nitropropionic acid
3-Nitropropionic acid, 8CI
3-NP acid
3-NPA
504-88-1 (FREE ACID)
beta -nitropropionic acid
beta-Nitropropanoate
beta-Nitropropanoic acid
beta-Nitropropionic acid
BNP
Hiptagenic acid
Nitropropionic acid, beta
NSC 64266
Propanoic acid, 3-nitro- (9CI)

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

InChIKey=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
LogP	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	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	splash10-00di-9100000000-c84646547cc314df783e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9500000000-ff7957d32f819292d644	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-2900000000-b06f8e6c082d20a54d6e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9100000000-08c8f64733feed89812a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bti-9000000000-ef962de7ab2944fcaa9f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-7900000000-d8fc1c7d184d25bb9c5b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uki-9500000000-9efcc70c860c5ed1033a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9000000000-28a52986668d447dc00b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9700000000-7764bae0c8f7785cb8ee	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-39537a3c0fd0f755292a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9000000000-94855126f2f5e14340d1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00r2-9700000000-171d4328fbe5a0ba1cb4	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-17277526de0706b5782c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

16348

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

3NP

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Olsen C, Rustad A, Fonnum F, Paulsen RE, Hassel B: 3-Nitropropionic acid: an astrocyte-sparing neurotoxin in vitro. Brain Res. 1999 Dec 11;850(1-2):144-9. [10629758 ]
Huang LS, Sun G, Cobessi D, Wang AC, Shen JT, Tung EY, Anderson VE, Berry EA: 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006 Mar 3;281(9):5965-72. Epub 2005 Dec 21. [16371358 ]
Kumar P, Kalonia H, Kumar A: Novel protective mechanisms of antidepressants against 3-nitropropionic acid induced Huntington's-like symptoms: a comparative study. J Psychopharmacol. 2011 Oct;25(10):1399-411. doi: 10.1177/0269881110364269. Epub 2010 Mar 19. [20305041 ]
Chomcheon P, Wiyakrutta S, Sriubolmas N, Ngamrojanavanich N, Isarangkul D, Kittakoop P: 3-Nitropropionic acid (3-NPA), a potent antimycobacterial agent from endophytic fungi: is 3-NPA in some plants produced by endophytes? J Nat Prod. 2005 Jul;68(7):1103-5. [16038559 ]
Borlongan CV, Koutouzis TK, Sanberg PR: 3-Nitropropionic acid animal model and Huntington's disease. Neurosci Biobehav Rev. 1997 May;21(3):289-93. [9168265 ]
Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial

General Function:: Ubiquinone binding
Specific Function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHD
Uniprot ID:: O14521
Molecular Weight:: 17042.82 Da

References

Olsen C, Rustad A, Fonnum F, Paulsen RE, Hassel B: 3-Nitropropionic acid: an astrocyte-sparing neurotoxin in vitro. Brain Res. 1999 Dec 11;850(1-2):144-9. [10629758 ]
Huang LS, Sun G, Cobessi D, Wang AC, Shen JT, Tung EY, Anderson VE, Berry EA: 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006 Mar 3;281(9):5965-72. Epub 2005 Dec 21. [16371358 ]

Target Details

2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

General Function:: Succinate dehydrogenase activity
Specific Function:: Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:: SDHA
Uniprot ID:: P31040
Molecular Weight:: 72690.975 Da

References

Olsen C, Rustad A, Fonnum F, Paulsen RE, Hassel B: 3-Nitropropionic acid: an astrocyte-sparing neurotoxin in vitro. Brain Res. 1999 Dec 11;850(1-2):144-9. [10629758 ]
Huang LS, Sun G, Cobessi D, Wang AC, Shen JT, Tung EY, Anderson VE, Berry EA: 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006 Mar 3;281(9):5965-72. Epub 2005 Dec 21. [16371358 ]

Target Details

3. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial

General Function:: Ubiquinone binding
Specific Function:: Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHB
Uniprot ID:: P21912
Molecular Weight:: 31629.365 Da

References

Olsen C, Rustad A, Fonnum F, Paulsen RE, Hassel B: 3-Nitropropionic acid: an astrocyte-sparing neurotoxin in vitro. Brain Res. 1999 Dec 11;850(1-2):144-9. [10629758 ]
Huang LS, Sun G, Cobessi D, Wang AC, Shen JT, Tung EY, Anderson VE, Berry EA: 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006 Mar 3;281(9):5965-72. Epub 2005 Dec 21. [16371358 ]

Target Details

4. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial

General Function:: Succinate dehydrogenase activity
Specific Function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHC
Uniprot ID:: Q99643
Molecular Weight:: 18610.03 Da

References

Olsen C, Rustad A, Fonnum F, Paulsen RE, Hassel B: 3-Nitropropionic acid: an astrocyte-sparing neurotoxin in vitro. Brain Res. 1999 Dec 11;850(1-2):144-9. [10629758 ]
Huang LS, Sun G, Cobessi D, Wang AC, Shen JT, Tung EY, Anderson VE, Berry EA: 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006 Mar 3;281(9):5965-72. Epub 2005 Dec 21. [16371358 ]

Bovinocidin (T3D3724)

Structure for T3D3724: Bovinocidin

Targets

References

References

References

References