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Showing NP-Card for 1-nitro-2,3-dihydropyrrole (NP0184636)

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Record Information
Version1.0
Created at2022-09-03 23:48:41 UTC
Updated at2022-09-03 23:48:41 UTC
NP-MRD IDNP0184636
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-nitro-2,3-dihydropyrrole
DescriptionNitropyrrolin belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. It was first documented in 2005 (PMID: 15804538). Based on a literature review a small amount of articles have been published on nitropyrrolin (PMID: 21090803) (PMID: 29534540) (PMID: 30270625) (PMID: 28898092).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0184636 (1-nitro-2,3-dihydropyrrole)


  Mrv1652309042201482D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
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3D MOL for NP0184636 (1-nitro-2,3-dihydropyrrole)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7733    0.3143    0.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -0.0768   -0.0455 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.8526   -0.6695   -1.0580 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.7487    0.0453   -0.1803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185    1.2627   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2572    1.0196    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825   -0.4193    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -1.0241   -0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4200    2.2057   -0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    1.7236    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1157   -0.5360    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3627   -0.8382    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100   -1.9721    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -1.0350   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  8 13  1  0
  8 14  1  0
  7 11  1  0
  7 12  1  0
  6 10  1  0
  5  9  1  0
M  CHG  2   2   1   3  -1
M  END
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3D SDF for NP0184636 (1-nitro-2,3-dihydropyrrole)


  Mrv1652309042201482D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0184636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+](=O)N1CCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2O2/c7-6(8)5-3-1-2-4-5/h1,3H,2,4H2

> <INCHI_KEY>
INHYCNGBUDCDQQ-UHFFFAOYSA-N

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.104

> <EXACT_MASS>
114.042927441

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.140519157870152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-nitro-2,3-dihydro-1H-pyrrole

> <JCHEM_LOGP>
-1.2605385674717449

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
46.38

> <JCHEM_REFRACTIVITY>
28.4317

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-nitro-2,3-dihydropyrrole

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0184636 (1-nitro-2,3-dihydropyrrole)

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PDB for NP0184636 (1-nitro-2,3-dihydropyrrole)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       1.060   3.620   0.000  0.00  0.00           N+1
HETATM    3  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O-1
HETATM    4  N   UNK     0       1.060   2.080   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0184636 (1-nitro-2,3-dihydropyrrole)
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SMILES for NP0184636 (1-nitro-2,3-dihydropyrrole)
[O-][N+](=O)N1CCC=C1
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INCHI for NP0184636 (1-nitro-2,3-dihydropyrrole)
InChI=1S/C4H6N2O2/c7-6(8)5-3-1-2-4-5/h1,3H,2,4H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC4H6N2O2
Average Mass114.1040 Da
Monoisotopic Mass114.04293 Da
IUPAC Name1-nitro-2,3-dihydro-1H-pyrrole
Traditional Name1-nitro-2,3-dihydropyrrole
CAS Registry NumberNot Available
SMILES
[O-][N+](=O)N1CCC=C1
InChI Identifier
InChI=1S/C4H6N2O2/c7-6(8)5-3-1-2-4-5/h1,3H,2,4H2
InChI KeyINHYCNGBUDCDQQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolines  
Sub ClassNot Available
Direct ParentPyrrolines  
Alternative Parents
Substituents
  • Pyrroline
    • 

  • Organic nitro compound
    • 

  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

  • Allyl-type 1,3-dipolar organic compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organonitrogen compound
    • 

  • Organic cation
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.43 m³·mol⁻¹ChemAxon
Polarizability10.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID67174060  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90703052  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kwon HC, Espindola AP, Park JS, Prieto-Davo A, Rose M, Jensen PR, Fenical W: Nitropyrrolins A-E, cytotoxic farnesyl-alpha-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae. J Nat Prod. 2010 Dec 27;73(12):2047-52. doi: 10.1021/np1006229. Epub 2010 Nov 23. [PubMed:21090803  ] 
  2. Park JS, Kwon HC: New Naphthoquinone Terpenoids from Marine Actinobacterium, Streptomyces sp. CNQ-509. Mar Drugs. 2018 Mar 12;16(3). pii: md16030090. doi: 10.3390/md16030090. [PubMed:29534540  ] 
  3. Ding XB, Brimble MA, Furkert DP: Reactivity of 2-Nitropyrrole Systems: Development of Improved Synthetic Approaches to Nitropyrrole Natural Products. J Org Chem. 2018 Oct 19;83(20):12460-12470. doi: 10.1021/acs.joc.8b01692. Epub 2018 Oct 10. [PubMed:30270625  ] 
  4. Ding XB, Furkert DP, Brimble MA: General Synthesis of the Nitropyrrolin Family of Natural Products via Regioselective CO(2)-Mediated Alkyne Hydration. Org Lett. 2017 Oct 6;19(19):5418-5421. doi: 10.1021/acs.orglett.7b02687. Epub  2017 Sep 12. [PubMed:28898092  ] 
  5. Poschenrieder H, Stachel HD, Hofner G, Mayer P: Novel pyrrolinones as N-methyl-D-aspartate receptor antagonists. Eur J Med Chem. 2005 Apr;40(4):391-400. doi: 10.1016/j.ejmech.2004.11.010. [PubMed:15804538  ] 
  6. LOTUS database [Link]