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504-88-1

504-88-1 | 3-Nitropropionic acid

CAS No: 504-88-1 Catalog No: AG003JTU MDL No:MFCD00007406

Product Description

Catalog Number:
AG003JTU
Chemical Name:
3-Nitropropionic acid
CAS Number:
504-88-1
Molecular Formula:
C3H5NO4
Molecular Weight:
119.0761
MDL Number:
MFCD00007406
IUPAC Name:
3-nitropropanoic acid
InChI:
InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)
InChI Key:
WBLZUCOIBUDNBV-UHFFFAOYSA-N
SMILES:
[O-][N+](=O)CCC(=O)O
EC Number:
208-003-0
UNII:
QY4L0FOX0D
NSC Number:
64266
UN Number:
2811

Properties

Complexity:
104  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
119.022g/mol
Formal Charge:
0
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
119.076g/mol
Monoisotopic Mass:
119.022g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
83.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.5  

Literature

Title Journal
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Mitochondrial inhibitor models of Huntington's disease and Parkinson's disease induce zinc accumulation and are attenuated by inhibition of zinc neurotoxicity in vitro or in vivo. Neuro-degenerative diseases 20130101
Naringin modulates oxidative stress and inflammation in 3-nitropropionic acid-induced neurodegeneration through the activation of nuclear factor-erythroid 2-related factor-2 signalling pathway. Neuroscience 20121227
The NMDA receptor subunit GluN3A protects against 3-nitroproprionic-induced striatal lesions via inhibition of calpain activation. Neurobiology of disease 20121201
Antibiotic susceptibility profile of Mycobacterium avium subspecies hominissuis is altered in low-iron conditions. The Journal of antimicrobial chemotherapy 20121201
Catechins protect neurons against mitochondrial toxins and HIV proteins via activation of the BDNF pathway. Journal of neurovirology 20121201
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Dithiol-based compounds maintain expression of antioxidant protein peroxiredoxin 1 that counteracts toxicity of mutant huntingtin. The Journal of biological chemistry 20120629
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Pretreatment with Bacopa monnieri extract offsets 3-nitropropionic acid induced mitochondrial oxidative stress and dysfunctions in the striatum of prepubertal mouse brain. Canadian journal of physiology and pharmacology 20120501
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Bioactive lipids from the sponge Spirastrella abata. Bioorganic & medicinal chemistry letters 20120115
Downregulation of miR-199a may play a role in 3-nitropropionic acid induced ischemic tolerance in rat brain. Brain research 20120106
Early alterations of brain cellular energy homeostasis in Huntington disease models. The Journal of biological chemistry 20120106
Peroxisome proliferator-activated receptor-α activation attenuates 3-nitropropionic acid induced behavioral and biochemical alterations in rats: possible neuroprotective mechanisms. European journal of pharmacology 20120105
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Bmi1 is down-regulated in the aging brain and displays antioxidant and protective activities in neurons. PloS one 20120101
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α-Mangostin induces apoptosis and suppresses differentiation of 3T3-L1 cells via inhibiting fatty acid synthase. PloS one 20120101
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Melatonin improves 3-nitropropionic acid induced behavioral alterations and neurotrophic factors levels. Progress in neuro-psychopharmacology & biological psychiatry 20111201
Neuroprotective effect of naringin, a dietary flavonoid against 3-nitropropionic acid-induced neuronal apoptosis. Neurochemistry international 20111201
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The effect of Ginkgo biloba extract on 3-nitropropionic acid-induced neurotoxicity in rats. Neurochemistry international 20111101
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FK506 ameliorates cell death features in Huntington's disease striatal cell models. Neurochemistry international 20111001
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Engrailed protects mouse midbrain dopaminergic neurons against mitochondrial complex I insults. Nature neuroscience 20110904
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Lycopene prevents 3-nitropropionic acid-induced mitochondrial oxidative stress and dysfunctions in nervous system. Neurochemistry international 20101101
Possible nitric oxide modulation in protective effect of FK-506 against 3-nitropropionic acid-induced behavioral, oxidative, neurochemical, and mitochondrial alterations in rat brain. Drug and chemical toxicology 20101001
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Brain region specificity of 3-nitropropionic acid-induced vulnerability of neurons involves cytochrome c oxidase. Neurochemistry international 20101001
Kainic acid and 3-Nitropropionic acid induced expression of laminin in vascular elements of the rat brain. Brain research 20100917
Androgens selectively protect against apoptosis in hippocampal neurones. Journal of neuroendocrinology 20100901
Inhibition of transglutaminase 2 mitigates transcriptional dysregulation in models of Huntington disease. EMBO molecular medicine 20100901
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The role of mitochondria in brain aging and the effects of melatonin. Current neuropharmacology 20100901
Assessment of 3-nitropropionic acid-evoked peripheral neuropathy in rats: neuroprotective effects of acetyl-l-carnitine and resveratrol. Neuroscience letters 20100816
Regulation of GSK-3beta by calpain in the 3-nitropropionic acid model. Hippocampus 20100801
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Delayed pre-conditioning by 3-nitropropionic acid prevents 3,4-methylenedioxymetamphetamine-induced 5-HT deficits. Journal of neurochemistry 20100801
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Protective effect of sesamol against 3-nitropropionic acid-induced cognitive dysfunction and altered glutathione redox balance in rats. Basic & clinical pharmacology & toxicology 20100701
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Ketones prevent synaptic dysfunction induced by mitochondrial respiratory complex inhibitors. Journal of neurochemistry 20100701
Cystamine protects from 3-nitropropionic acid lesioning via induction of nf-e2 related factor 2 mediated transcription. Experimental neurology 20100701
Mechanisms underlying striatal vulnerability to 3-nitropropionic acid. Journal of neurochemistry 20100701
Brain region-specific vulnerability of astrocytes in response to 3-nitropropionic acid is mediated by cytochrome c oxidase isoform expression. Cell and tissue research 20100701
Neuroprotective mechanisms of brain-derived neurotrophic factor against 3-nitropropionic acid toxicity: therapeutic implications for Huntington's disease. Annals of the New York Academy of Sciences 20100701
Lithium reduces apoptosis and autophagy after neonatal hypoxia-ischemia. Cell death & disease 20100701
Prophylaxis with Centella asiatica confers protection to prepubertal mice against 3-nitropropionic-acid-induced oxidative stress in brain. Phytotherapy research : PTR 20100601
FoxO1 is involved in the antineoplastic effect of calorie restriction. Aging cell 20100601
Geranylgeranylacetone ameliorates acute cochlear damage caused by 3-nitropropionic acid. Neurotoxicology 20100601
Mitochondrial matters of the brain: the role in Huntington's disease. Journal of bioenergetics and biomembranes 20100601
Dysregulation of CREB activation and histone acetylation in 3-nitropropionic acid-treated cortical neurons: prevention by BDNF and NGF. Neurotoxicity research 20100501
Balance dysfunction resulting from acute inner ear energy failure is caused primarily by vestibular hair cell damage. Journal of neuroscience research 20100501
Sildenafil protects against 3-nitropropionic acid neurotoxicity through the modulation of calpain, CREB, and BDNF. Neurobiology of disease 20100501
Nitric oxide mechanism in the protective effect of antidepressants against 3-nitropropionic acid-induced cognitive deficit, glutathione and mitochondrial alterations in animal model of Huntington's disease. Behavioural pharmacology 20100501
Alpha-synuclein deficient mice are resistant to toxin-induced multiple system atrophy. Neuroreport 20100421
Opening of the mitoKATP channel and decoupling of mitochondrial complex II and III contribute to the suppression of myocardial reperfusion hyperoxygenation. Molecular and cellular biochemistry 20100401
Mitochondrial-dependent apoptosis in Huntington's disease human cybrids. Experimental neurology 20100401
Hypoxia sensing in the fetal chicken femoral artery is mediated by the mitochondrial electron transport chain. American journal of physiology. Regulatory, integrative and comparative physiology 20100401
Mitochondrial quality control and neurological disease: an emerging connection. Expert reviews in molecular medicine 20100401
HIF prolyl hydroxylase inhibitors prevent neuronal death induced by mitochondrial toxins: therapeutic implications for Huntington's disease and Alzheimer's disease. Antioxidants & redox signaling 20100215
3-nitropropionic acid-induced mitochondrial permeability transition: comparative study of mitochondria from different tissues and brain regions. Journal of neuroscience research 20100215
3-Nitropropionic acid as a tool to study the mechanisms involved in Huntington's disease: past, present and future. Molecules (Basel, Switzerland) 20100210
Systemic administration of 3-nitropropionic acid points out a different role for active caspase-3 in neurons and astrocytes. Neurochemistry international 20100201
Enhanced expression of C/EBP homologous protein (CHOP) precedes degeneration of fibrocytes in the lateral wall after acute cochlear mitochondrial dysfunction induced by 3-nitropropionic acid. Neurochemistry international 20100201
Protective effect of hesperidin and naringin against 3-nitropropionic acid induced Huntington's like symptoms in rats: possible role of nitric oxide. Behavioural brain research 20100105
Trolox ameliorates 3-nitropropionic acid-induced neurotoxicity in rats. Neurotoxicology and teratology 20100101
Protective effect of tert-butylhydroquinone on the quinolinic-acid-induced toxicity in rat striatal slices: role of the Nrf2-antioxidant response element pathway. Neuro-Signals 20100101
Discriminative behavioral assessment unveils remarkable reactive astrocytosis and early molecular correlates in basal ganglia of 3-nitropropionic acid subchronic treated rats. Neurochemistry international 20100101
Promethazine protects against 3-nitropropionic acid-induced neurotoxicity. Neurochemistry international 20100101
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The role of mitochondria in protection of the heart by preconditioning. Biochimica et biophysica acta 20070801
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Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20070718
Creatine treatment promotes differentiation of GABA-ergic neuronal precursors in cultured fetal rat spinal cord. Journal of neuroscience research 20070701
Mesenchymal stem cell transplantation accelerates hearing recovery through the repair of injured cochlear fibrocytes. The American journal of pathology 20070701
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Ubiquitin-proteasome system alterations in a striatal cell model of Huntington's disease. Journal of neuroscience research 20070601
Manganese targets m-aconitase and activates iron regulatory protein 2 in AF5 GABAergic cells. Journal of neuroscience research 20070601
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Mutant SOD1G93A in bone marrow-derived cells exacerbates 3-nitropropionic acid induced striatal damage in mice. Neuroscience letters 20070517
Neurturin gene therapy improves motor function and prevents death of striatal neurons in a 3-nitropropionic acid rat model of Huntington's disease. Neurobiology of disease 20070501
Effect of testosterone on oxidative stress and cell damage induced by 3-nitropropionic acid in striatum of ovariectomized rats. Life sciences 20070306
Gender- and region-specific expression of insulin receptor protein in mouse brain: effect of mild inhibition of oxidative phosphorylation. Journal of neural transmission (Vienna, Austria : 1996) 20070301
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Pharmacological MRI of stem cell transplants in the 3-nitropropionic acid-damaged striatum. Neuroscience 20070105
Transglutaminase 2 ablation leads to defective function of mitochondrial respiratory complex I affecting neuronal vulnerability in experimental models of extrapyramidal disorders. Journal of neurochemistry 20070101
Mitochondrial toxins and neurodegenerative diseases. Frontiers in bioscience : a journal and virtual library 20070101
Integrative hypothesis for Huntington's disease: a brief review of experimental evidence. Physiological research 20070101
Evidence of ROS generation by mitochondria in cells with impaired electron transport chain and mitochondrial DNA damage. Mitochondrion 20070101
Proteasome activator enhances survival of Huntington's disease neuronal model cells. PloS one 20070101
Possible neuroprotective mechanisms of curcumin in attenuating 3-nitropropionic acid-induced neurotoxicity. Methods and findings in experimental and clinical pharmacology 20070101
Sequence variation in human succinate dehydrogenase genes: evidence for long-term balancing selection on SDHA. BMC biology 20070101
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Hyperglycemia enhances the inhibitory effect of mitochondrial toxins and D,L-homocysteine on the brain production of kynurenic acid. Pharmacological reports : PR 20070101
Early energy deficit in Huntington disease: identification of a plasma biomarker traceable during disease progression. PloS one 20070101
Identification of gene targets against dormant phase Mycobacterium tuberculosis infections. BMC infectious diseases 20070101
The responses of HT22 cells to the blockade of mitochondrial complexes and potential protective effect of selenium supplementation. International journal of biological sciences 20070101
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The functional genome of CA1 and CA3 neurons under native conditions and in response to ischemia. BMC genomics 20070101
Developmental stage of oligodendrocytes determines their response to activated microglia in vitro. Journal of neuroinflammation 20070101
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MEK inhibition exacerbates ischemic calcium imbalance and neuronal cell death in rat cortical cultures. European journal of pharmacology 20061228
Co-regulation of dopamine D1 receptor and uncoupling protein-2 expression in 3-nitropropionic acid-induced neurotoxicity: neuroprotective role of L-carnitine. Neuroscience letters 20061213
Deficits of glutamate transmission in the striatum of toxic and genetic models of Huntington's disease. Neuroscience letters 20061213
NR2B-containing NMDA receptors promote the neurotoxic effects of 3-nitropropionic acid but not of rotenone in the striatum. Experimental neurology 20061201
Acute administration of 3-nitropropionic acid, a reactive oxygen species generator, boosts ethanol-induced locomotor stimulation. New support for the role of brain catalase in the behavioural effects of ethanol. Neuropharmacology 20061201
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