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3-Nitropropanoic acid (Standard)

CAT: 0804-HY-W012875R-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W012875R-01Size:10 mg
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Description
3-Nitropropanoic acid (Standard) is the analytical standard of 3-Nitropropanoic acid. This product is intended for research and analytical applications. 3-Nitropropanoic acid (β-Nitropropionic acid) is an irreversible and orally active inhibitor of succinate dehydrogenase. 3-Nitropropanoic acid exhibits potent antimycobacterial activity with a MIC value of 3.3 μM. 3-Nitropropanoic acid can induce cell apoptosis[1][2].
CAS Number
504-88-1
Product Name Alternative
β-Nitropropionic acid (Standard) ; Bovinocidin (Standard)
UNSPSC
12352211
Target
Apoptosis; Autophagy; Bacterial; Reference Standards
Related Pathways
Anti-infection; Apoptosis; Autophagy; Others
Field of Research
Infection; Metabolic Disease
Smiles
O=C(O)CC[N+]([O-])=O
Molecular Formula
C3H5NO4
Molecular Weight
119.08
References & Citations
[1]Huang LS, et al. 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.|[2]Chomcheon P, et al. 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.|[3]Solesio ME, et al. 3-Nitropropionic acid induces autophagy by forming mitochondrial permeability transition pores rather than activating the mitochondrial fission pathway. Br J Pharmacol. 2013 Jan;168 (1) :63-75.|[4]Kang B, et al. Effect of 3-nitropropionic acid inducing oxidative stress and apoptosis of granulosa cells in geese. Biosci Rep. 2018 Sep 12;38 (5) :BSR20180274.|[5]Pang Z, Geddes JW. Mechanisms of cell death induced by the mitochondrial toxin 3-nitropropionic acid: acute excitotoxic necrosis and delayed apoptosis. J Neurosci. 1997 May 1;17 (9) :3064-73.|[6]Túnez I, et al. Protective effect of melatonin on 3-nitropropionic acid-induced oxidative stress in synaptosomes in an animal model of Huntington's disease. J Pineal Res. 2004 Nov;37 (4) :252-6.|[7]Urbanska EM, et al. A. Mitochondrial toxin 3-nitropropionic acid evokes seizures in mice. Eur J Pharmacol. 1998 Oct 16;359 (1) :55-8.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

3-Nitropropionic acid

3-nitropropanoic acid is a C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group. It has a role as a mycotoxin, a neurotoxin, an antimycobacterial drug and an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor. It is functionally related to a propionic acid. It is a conjugate acid of a 3-nitropropanoate. It is a tautomer of a 3-aci-nitropropanoic acid.

CAS Number504-88-1
PubChem CID1678
IUPAC Name3-nitropropanoic acid
Molecular FormulaC3H5NO4
Molecular Weight119.08
XLogP-0.5
Topological Polar Surface Area83.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count8
Formal Charge0
Complexity104
SMILES
C(C[N+](=O)[O-])C(=O)O
InChI
InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)
InChIKey
WBLZUCOIBUDNBV-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 3-Nitropropionic acid
CAS: 504-88-1
CID: 1678
Formula: C3H5NO4
MW: 119.08
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight119.08
XLogP3-0.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass119.02185764
Monoisotopic Mass119.02185764
Topological Polar Surface Area83.1 Ų
Heavy Atom Count8
Formal Charge0
Complexity104
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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