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Showing NP-Card for 2-methylidenepyrrole (NP0180175)

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Record Information
Version1.0
Created at2022-09-03 18:29:58 UTC
Updated at2022-09-03 18:29:58 UTC
NP-MRD IDNP0180175
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-methylidenepyrrole
DescriptionAzafulvene belongs to the class of organic compounds known as azacyclic compounds. These are organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other. 2-methylidenepyrrole is found in Euglena gracilis. It was first documented in 2019 (PMID: 31891109). Based on a literature review a significant number of articles have been published on azafulvene (PMID: 33186819) (PMID: 33006344) (PMID: 32330033) (PMID: 30855607).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0180175 (2-methylidenepyrrole)


  Mrv1652309032220292D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   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 N   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
M  END
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3D MOL for NP0180175 (2-methylidenepyrrole)

     RDKit          3D

 11 11  0  0  0  0  0  0  0  0999 V2000
    1.9962   -0.2490   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -0.2148   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    0.9635    0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    0.5405    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4564   -0.8863   -0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -1.2942   -0.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -1.1724   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348    0.6720    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960    1.9847    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041    1.1420    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731   -1.4860   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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3D SDF for NP0180175 (2-methylidenepyrrole)


  Mrv1652309032220292D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   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 N   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=C1C=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N/c1-5-3-2-4-6-5/h2-4H,1H2

> <INCHI_KEY>
LVFHXTSDKGRPEJ-UHFFFAOYSA-N

> <FORMULA>
C5H5N

> <MOLECULAR_WEIGHT>
79.102

> <EXACT_MASS>
79.042199165

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.42082308917854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidene-2H-pyrrole

> <JCHEM_LOGP>
0.45531534799999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.91308734710255

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
27.269399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-methylidenepyrrole

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0180175 (2-methylidenepyrrole)

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PDB for NP0180175 (2-methylidenepyrrole)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0180175 (2-methylidenepyrrole)
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SMILES for NP0180175 (2-methylidenepyrrole)
C=C1C=CC=N1
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INCHI for NP0180175 (2-methylidenepyrrole)
InChI=1S/C5H5N/c1-5-3-2-4-6-5/h2-4H,1H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC5H5N
Average Mass79.1020 Da
Monoisotopic Mass79.04220 Da
IUPAC Name2-methylidene-2H-pyrrole
Traditional Name2-methylidenepyrrole
CAS Registry NumberNot Available
SMILES
C=C1C=CC=N1
InChI Identifier
InChI=1S/C5H5N/c1-5-3-2-4-6-5/h2-4H,1H2
InChI KeyLVFHXTSDKGRPEJ-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 Origin
Species NameSourceReference
Euglena gracilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as azacyclic compounds. These are organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzacyclic compounds  
Sub ClassNot Available
Direct ParentAzacyclic compounds  
Alternative Parents
Substituents
  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

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

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Imine
    • 

  • 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
logP0.46ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.27 m³·mol⁻¹ChemAxon
Polarizability8.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24771845  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound66958297  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wu Q, Wang S, Hao E, Jiao L: Highly selective, colorimetric probes for cyanide ion based on beta-formylBODIPY dyes by an unprecedented nucleophilic addition reaction. Spectrochim Acta A Mol Biomol Spectrosc. 2021 Feb 15;247:119102. doi:  10.1016/j.saa.2020.119102. Epub 2020 Nov 4. [PubMed:33186819  ] 
  2. Kumar R, Guchhait T, Subramaniyan V, Schulzke C, Mani G: Versatility of the bis(iminopyrrolylmethyl)amine ligand: tautomerism, protonation, helical chirality, and the secondary coordination sphere with halogen bonds in the formation of copper(II) and nickel(II) complexes. Dalton Trans. 2020 Oct 12;49(39):13840-13853. doi: 10.1039/d0dt02964e. [PubMed:33006344  ] 
  3. Kim H, Brooks AD, DiLauro AM, Phillips ST: Poly(carboxypyrrole)s That Depolymerize from Head to Tail in the Solid State in Response to Specific Applied Signals. J Am Chem Soc. 2020 May 20;142(20):9447-9452. doi: 10.1021/jacs.0c02774. Epub  2020 May 8. [PubMed:32330033  ] 
  4. Kua J, Miller AS, Wallace CE, Loli H: Role of Acid in the Co-oligomerization of Formaldehyde and Pyrrole. ACS Omega. 2019 Dec 9;4(26):22251-22259. doi: 10.1021/acsomega.9b03931.  eCollection 2019 Dec 24. [PubMed:31891109  ] 
  5. Wang J, Zhao YY, Lee PH, Wu K: Computational analysis of non-heme iron-oxo formation by direct NO release in nitrite reduction. Phys Chem Chem Phys. 2019 Mar 28;21(12):6643-6650. doi: 10.1039/c9cp00370c. Epub  2019 Mar 11. [PubMed:30855607  ] 
  6. LOTUS database [Link]