Bovinocidin
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Basic Info
| Common Name | Bovinocidin(F04971) |
| 2D Structure | |
| 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. |
| FRCD ID | F04971 |
| CAS Number | 504-88-1 |
| PubChem CID | 1678 |
| Formula | C3H5NO4 |
| IUPAC Name | None |
| InChI Key | WBLZUCOIBUDNBV-UHFFFAOYSA-N |
| InChI | InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6) |
| Canonical SMILES | C(C[N+](=O)[O-])C(=O)O |
| Isomeric SMILES | C(C[N+](=O)[O-])C(=O)O |
| Synonyms |
3-nitropropionic acid
3-Nitropropanoic acid
504-88-1
Bovinocidin
Hiptagenic acid
Propanoic acid, 3-nitro-
beta-Nitropropionic acid
3-Nitropropionate
Propionic acid, 3-nitro-
beta-Nitropropanoic acid
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic 1,3-dipolar compounds |
| Class | Allyl-type 1,3-dipolar organic compounds |
| Subclass | Organic nitro compounds |
| Intermediate Tree Nodes | Not available |
| Direct Parent | C-nitro compounds |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as c-nitro compounds. These are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 119.076 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 104 |
| Monoisotopic Mass | 119.022 |
| Exact Mass | 119.022 |
| XLogP | -0.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Bacterial species and mycotoxin contamination associated with locust bean, melon and their fermented products in south-western Nigeria. | Int J Food Microbiol | 2017 Oct 3 | 28759798 |
| Characterization of age-dependent changes in the striatum: Response to themitochondrial toxin 3-nitropropionic acid. | Mech Ageing Dev | 2017 Jan | 27143313 |
| Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 25350522 |
| Fungal and bacterial metabolites associated with natural contamination of locally processed rice (Oryza sativa L.) in Nigeria. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 25767914 |
| Neuromodulatory propensity of Bacopa monnieri leaf extract against3-nitropropionic acid-induced oxidative stress: in vitro and in vivo evidences. | Neurotox Res | 2012 Aug | 22203611 |
| L-carnitine and neuroprotection in the animal model of mitochondrial dysfunction. | Ann N Y Acad Sci | 2005 Aug | 16179521 |
| Neuroprotective effect of L-carnitine in the 3-nitropropionic acid (3-NPA)-evoked neurotoxicity in rats. | Neurosci Lett | 2004 Sep 2 | 15331167 |
| Production of toxic metabolites in Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei: justification of mycotoxin testing in food grade enzyme preparations derived from the three fungi. | Regul Toxicol Pharmacol | 2004 Apr | 15041150 |
| Beneficial effects of dietary restriction on cerebral cortical synapticterminals: preservation of glucose and glutamate transport and mitochondrialfunction after exposure to amyloid beta-peptide, iron, and 3-nitropropionic acid. | J Neurochem | 2000 Jul | 10854276 |
| [Quantitative determination of 3-nitropropionic acid by HPLC]. | Wei Sheng Yan Jiu | 1999 Sep 30 | 12712703 |
| Use of a flow cell bioreactor as a chronic toxicity model system. | Toxicol In Vitro | 1999 Aug-Oct | 20654559 |
| Delayed dystonia with striatal CT lucencies induced by a mycotoxin(3-nitropropionic acid). | Neurology | 1995 Dec | 8848189 |
Targets
- 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
- Mechanism of Action:
- 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.
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 ]
- 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
- Mechanism of Action:
- 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.
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 ]
- 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
- Mechanism of Action:
- 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.
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 ]
- 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
- Mechanism of Action:
- 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.
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 ]