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Showing NP-Card for β-nitropropionic acid (NP0005118)

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Record Information
Version1.0
Created at2020-12-09 02:27:40 UTC
Updated at2021-07-15 16:51:06 UTC
NP-MRD IDNP0005118
Secondary Accession NumbersNone
Natural Product Identification
Common Nameβ-nitropropionic acid
Provided ByNPAtlasNPAtlas Logo
DescriptionBovinocidin, also known as 3-nitropropionate or 3-NP acid, belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. Bovinocidin exists in all living organisms, ranging from bacteria to humans. Bovinocidin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. β-nitropropionic acid is found in Aspergillus flavus, Securigera varia, Indigofera suffruticosa, Penicillium atrovenetum and Phomopsis velata. It was first documented in 1951 (PMID: 14824156). Based on a literature review a significant number of articles have been published on Bovinocidin (PMID: 11409756) (PMID: 11785916) (PMID: 14700739) (PMID: 16038559).
Structure
Data?1624574306
MOL3D MOLSDF3D SDFPDBSMILESInChI

MOL for NP0005118 (β-nitropropionic acid)


  Mrv1652306242118173D          

 13 12  0  0  0  0            999 V2000
   -2.5561   -0.5680    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.0019   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    1.3682   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -0.8919   -0.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9980   -0.2551   -0.5039 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5449    0.5258    0.5477 N   0  3  0  0  0  4  0  0  0  0  0  0
    2.6357    0.2332    1.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    1.6319    1.0078 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.1109    1.8657    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.4439   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -1.6706    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.2958   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -1.0892   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
Download

3D MOL for NP0005118 (β-nitropropionic acid)

     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.5561   -0.5680    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.0019   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    1.3682   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -0.8919   -0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.2551   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    0.5258    0.5477 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6357    0.2332    1.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    1.6319    1.0078 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1109    1.8657    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.4439   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -1.6706    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.2958   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -1.0892   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
M  CHG  2   6   1   8  -1
M  END
Download

3D SDF for NP0005118 (β-nitropropionic acid)


  Mrv1652306242118173D          

 13 12  0  0  0  0            999 V2000
   -2.5561   -0.5680    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.0019   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    1.3682   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -0.8919   -0.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9980   -0.2551   -0.5039 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5449    0.5258    0.5477 N   0  3  0  0  0  4  0  0  0  0  0  0
    2.6357    0.2332    1.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    1.6319    1.0078 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.1109    1.8657    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.4439   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -1.6706    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.2958   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -1.0892   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
> <DATABASE_ID>
NP0005118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)

> <INCHI_KEY>
WBLZUCOIBUDNBV-UHFFFAOYSA-N

> <FORMULA>
C3H5NO4

> <MOLECULAR_WEIGHT>
119.0761

> <EXACT_MASS>
119.021857653

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.417210188885983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-nitropropanoic acid

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-0.2654693123333335

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.15040172327729

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.302468029319448

> <JCHEM_POLAR_SURFACE_AREA>
83.12

> <JCHEM_REFRACTIVITY>
23.3716

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-nitropropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0005118 (β-nitropropionic acid)

     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.5561   -0.5680    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.0019   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    1.3682   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -0.8919   -0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.2551   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    0.5258    0.5477 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6357    0.2332    1.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    1.6319    1.0078 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1109    1.8657    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.4439   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -1.6706    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.2958   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -1.0892   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
M  CHG  2   6   1   8  -1
M  END
Download

PDB for NP0005118 (β-nitropropionic acid)

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.556  -0.568   0.273  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.446  -0.002  -0.014  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.459   1.368  -0.039  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.316  -0.892  -0.275  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.998  -0.255  -0.504  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.545   0.526   0.548  0.00  0.00           N+1
HETATM    7  O   UNK     0       2.636   0.233   1.084  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.888   1.632   1.008  0.00  0.00           O-1
HETATM    9  H   UNK     0      -2.111   1.866   0.552  0.00  0.00           H+0
HETATM   10  H   UNK     0      -0.580  -1.444  -1.229  0.00  0.00           H+0
HETATM   11  H   UNK     0      -0.274  -1.671   0.538  0.00  0.00           H+0
HETATM   12  H   UNK     0       0.944   0.296  -1.481  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.731  -1.089  -0.731  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    9                                                       
CONECT    4    2    5   10   11                                             
CONECT    5    4    6   12   13                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
Download

3D PDB for NP0005118 (β-nitropropionic acid)

Download
SMILES for NP0005118 (β-nitropropionic acid)
[H]OC(=O)C([H])([H])C([H])([H])[N+]([O-])=O
Download
INCHI for NP0005118 (β-nitropropionic acid)
InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)
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View in JSmolView NMR Assignments
Synonyms
ValueSource
3-Nitropropionic acidChEBI
beta-Nitropropanoic acidChEBI
beta-Nitropropionic acidChEBI
3-NitropropanoateKegg
3-NitropropionateGenerator
b-NitropropanoateGenerator
b-Nitropropanoic acidGenerator
beta-NitropropanoateGenerator
Β-nitropropanoateGenerator
Β-nitropropanoic acidGenerator
b-NitropropionateGenerator
b-Nitropropionic acidGenerator
beta-NitropropionateGenerator
Β-nitropropionateGenerator
Β-nitropropionic acidGenerator
3-Nitropropanoic acidGenerator
3-Nitro-1-propionateHMDB
3-Nitro-propanoic acidHMDB
3-Nitro-propionic acidHMDB
3-Nitropropionic acid, 8ciHMDB
3-NP acidHMDB
3-NPAHMDB
504-88-1 (FREE acid)HMDB
beta -Nitropropionic acidHMDB
BNPHMDB
Hiptagenic acidHMDB
Nitropropionic acid, betaHMDB
NSC 64266HMDB
Propanoic acid, 3-nitro- (9ci)HMDB
Propionate 3-nitronateHMDB
BovinocidinChEBI
Chemical FormulaC3H5NO4
Average Mass119.0761 Da
Monoisotopic Mass119.02186 Da
IUPAC Name3-nitropropanoic acid
Traditional Nameβ-nitropropionic acid
CAS Registry NumberNot Available
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 KeyWBLZUCOIBUDNBV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus flavusNPAtlas
Coronilla variaLOTUS Database
Indigofera suffruticosaLOTUS Database
Penicillium atrovenetumLOTUS Database
Phomopsis velataLOTUS Database
Species Where Detected
Species NameSourceReference
Aspergillus sp.KNApSAcK Database
Aspergillus sp.dKNApSAcK Database
Streptomyces sp.KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon.
KingdomOrganic compounds
Super ClassOrganic 1,3-dipolar compounds
ClassAllyl-type 1,3-dipolar organic compounds
Sub ClassOrganic nitro compounds
Direct ParentC-nitro compounds
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.73ALOGPS
logP-0.27ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.12 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity23.37 m³·mol⁻¹ChemAxon
Polarizability9.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA007876  
HMDB IDHMDB0034259  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012579  
KNApSAcK IDC00018684  
Chemspider ID1615  
KEGG Compound IDC05669  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1678  
PDB IDNot Available
ChEBI ID16348  
Good Scents IDNot Available
References
General References
  1. BUSH MT, TOUSTER O, BROCKMAN JE: The production of beta-nitropropionic acid by a strain of Aspergillus flavus. J Biol Chem. 1951 Feb;188(2):685-93. [PubMed:14824156  ] 
  2. Blum D, Gall D, Cuvelier L, Schiffmann SN: Topological analysis of striatal lesions induced by 3-nitropropionic acid in the Lewis rat. Neuroreport. 2001 Jun 13;12(8):1769-72. doi: 10.1097/00001756-200106130-00050. [PubMed:11409756  ] 
  3. Zuchora B, Urbanska EM: Effect of adenosine receptor agonists on neurodegenerative and convulsive activity of mitochondrial toxin, 3-nitropropionic acid. Pol J Pharmacol. 2001 Jan-Feb;53(1):69-71. [PubMed:11785916  ] 
  4. Blum D, Galas MC, Cuvelier L, Schiffmann SN: Chronic intoxication with 3-nitropropionic acid in rats induces the loss of striatal dopamine terminals without affecting nigral cell viability. Neurosci Lett. 2004 Jan 16;354(3):234-8. doi: 10.1016/j.neulet.2003.10.034. [PubMed:14700739  ] 
  5. Chomcheon P, Wiyakrutta S, Sriubolmas N, Ngamrojanavanich N, Isarangkul D, Kittakoop P: 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. doi: 10.1021/np050036a. [PubMed:16038559  ]