Compound: 3-nitropropionic acid
SMILES: O=[N+]([O-])CCC(=O)O
InChIKey: WBLZUCOIBUDNBV-UHFFFAOYSA-N
Synonyms: 3-nitropropionic acid, 3-Nitropropanoic acid, 504-88-1, Bovinocidin, Hiptagenic acid, beta-Nitropropionic acid, Propanoic acid, 3-nitro-, Propionic acid, 3-nitro-, beta-Nitropropanoic acid, 3-NP acid, NCI-C03076, NSC 64266, NITROPROPIONIC ACID, BETA, DTXSID1020982, QY4L0FOX0D, CHEBI:16348, 3-nitro-1-propionate, NSC-64266, DTXCID10982, RefChem:504508, 208-003-0, 3-Nitropropionate, 3-NPA, MFCD00007406, 3-nitro-propionic acid, BOVINOCIDIN (3-nitropropionic acid), .beta.-Nitropropionic acid, beta-Nitropropanoate, BNP, CHEMBL451226, NSC64266, 3NP, CAS-504-88-1, CCRIS 454, HSDB 4147, Nitropropionic aci, beta, SR-01000076030, EINECS 208-003-0, UNII-QY4L0FOX0D, 3-NITROPROPIONICACID, BRN 1759889, BNP; Bovinocidin; Hiptagenic Acid; NSC 64266; ss-Nitropropionic Acid, 3-Nitroporpionic Acid, Spectrum_001674, 3-Nitro-Propanoic acid, SpecPlus_000692, beta -nitropropionic acid, Spectrum2_000876, Spectrum3_000993, Spectrum4_001119, Spectrum5_001895, Lopac-N-5636, WLN: WN2VQ, Nitropropionic acid, .beta., 3-Nitropropionic acid, 8CI, Lopac0_000838, SCHEMBL70072, BSPBio_002685, KBioGR_001598, KBioSS_002154, 4-02-00-00771 (Beilstein Handbook Reference), MLS001066410, 3-Nitropropionic acid, 97%, DivK1c_006788, SPECTRUM1504206, SPBio_000951, orb1304626, 3-Nitropropionic acid, >=97%, BDBM82201, KBio1_001732, KBio2_002154, KBio2_004722, KBio2_007290, KBio3_001905, MSK9132, GLXC-23573, HMS2235N03, HMS3262H17, HMS3369D16, HMS3865D03, Propanoic acid, 3-nitro- (9CI), Tox21_202460, Tox21_303007, Tox21_500838, BDBM50480795, CCG-40325, s3652, 3-NITROPROPIONIC ACID [HSDB], AKOS006221915, AKOS015833440, 504-88-1 (FREE ACID), CS-W013591, EBC-459059, FN15632, HY-W012875, LP00838, SDCCGMLS-0066769.P001, SDCCGSBI-0050815.P003, NCGC00015744-01, NCGC00015744-02, NCGC00015744-03, NCGC00015744-04, NCGC00015744-05, NCGC00015744-06, NCGC00015744-07, NCGC00015744-11, NCGC00094169-01, NCGC00094169-02, NCGC00094169-03, NCGC00094169-04, NCGC00256389-01, NCGC00260009-01, NCGC00261523-01, SMR000471863, SY110140, 3-Nitropropionic acid - CAS 504-88-1, DB-008848, EU-0100838, NS00032068, C05669, F17743, N 5636, F035948, Q223104, SR-01000076030-1, SR-01000076030-5
Theoretical properties:
molecular_formula: C3H5NO4
molecular_weight: 119.08 g/mol
exact_mass: 119.02185764 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 8
topological_polar_surface_area: 83.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from chloroform
color: Crystals from chloroform
melting_point: 145 to 149 °F (NTP, 1992)
solubility: greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
Descriptions:
pubchem: 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.
chebi: A <em>C</em>-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 3-Nitropropionic acid (3-NPA) is a mycotoxin which is severely toxic to humans. It is a potent suicidal inhibitor of succinate dehydrogenase, an enyzme in the citric acid cycle and mitochondrial energy chain. Mild cases of exposure give rise to nausea, vomiting, and stomach ache, while severe cases lead to brain damage or death. There is no known antidote to 3-nitropropionic acid poisoning.
3-nitropropionic acid is produced by a number of fungi, most notably in the Aspergillus family, and may be found in food such as in sugar cane as well as Japanese fungally fermented staples, including miso, soy sauce, katsuobushi, coconuts and some traditional Chinese medicines. Several outbreaks of 3-nitropropionic acid poisoning have been linked to contamination of shared food crops, particularly in China, where sugar cane is commonly consumed by children.