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T3D3724 - 3-Nitropropionic Acid
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2010-05-03 15:06:51 UTC |
| Update Date | 2013-04-25 08:48:45 UTC |
| Accession Number | T3D3724 |
| Identification | |
| Common Name | 3-Nitropropionic Acid |
| Description | 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. It is a suicide inhibitor of succinate dehydrogenase which affects the neurons by inhibiting the activity of the tricarboxylic acid (TCA) cycle as well as mitochondrial respiratory complex II of the electron transport chain. (W814, W815, W817) |
| Compound Type |
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| Chemical Structure |
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| Synonyms |
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| Chemical Formula | C3H5NO4 |
| Average Molecular Weight | 119.0761 |
| Monoisotopic Molecular Weight | 119.021857653 |
| Chemical IUPAC Name | 3-nitropropionic acid |
| CAS Registry Number | 504-88-1 |
| SMILES | OC(=O)CC[N+]([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 | |
| Kingdom | Organic Compounds |
| Super Class | Amino Acids, Peptides, and Analogues |
| Class | Amino Acids and Derivatives |
| Sub Class | Beta Amino Acids and Derivatives |
| Direct Parent | Beta Amino Acids and Derivatives |
| Alternative Parents |
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| Molecular Framework | Aliphatic Acyclic Compounds |
| Substituents |
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| External Descriptors |
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| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 1678  |
| KEGG ID | Not Available |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | 16348 |
| BioCyc ID | Not Available |
| CTD ID | Not Available |
| Stitch ID | Not Available |
| PDB ID | Not Available |
| ACToR ID | Not Available |
| Wikipedia Link | Not Available |
| Physical Properties | |
| Appearance | Not Available |
| Melting Point | Not Available |
| Solubility | Not Available |
| Predicted LogP | -0.2654693123333335 |
| Toxicity Profile | |
| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (W967) |
| 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. (W814, W815) |
| Metabolism | Not Available |
| Toxicity Values | Not Available |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| 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. (W814, W815, W817) |
| Minimum Risk Level | Not Available |
| Health Effects | 3-Nitropropionic acid causes neurodegeneration, particularity of the striatum, though also in the hippocampus and thalamus. (W814, W818) |
| Symptoms | 3-Nitropropionic acid causes symptoms similar to that of Huntington disease: motor and cognitive dysfunction that includes convulsions, dystonia, and hypokinesia. (W814, W816, W818) |
| Treatment | Not Available |
| References | |
| General References |
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Targets
1. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial
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).
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. (W814, W815)UniProt ID: Q99643
Gene: SDHC
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- W814 — 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 ]
- W815 — 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 ]
2. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
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) (By similarity).
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. (W814, W815)UniProt ID: O14521
Gene: SDHD
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- W814 — 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 ]
- W815 — 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 ]
3. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
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.
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. (W814, W815)UniProt ID: P31040
Gene: SDHA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- W814 — 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 ]
- W815 — 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 ]
4. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
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).
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. (W814, W815)UniProt ID: P21912
Gene: SDHB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- W814 — 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 ]
- W815 — 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 ]