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Showing NP-Card for Brunfelsamidine (NP0051119)

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Record Information
Version1.0
Created at2022-04-27 22:32:38 UTC
Updated at2022-04-27 22:32:39 UTC
NP-MRD IDNP0051119
Secondary Accession NumbersNone
Natural Product Identification
Common NameBrunfelsamidine
DescriptionBrunfelsamidine belongs to the class of organic compounds known as substituted pyrroles. These are heterocyclic compounds containing a pyrrole ring substituted at one or more positions. Brunfelsamidine is a very strong basic compound (based on its pKa). Brunfelsamidine is a poisonous plant derivative found in several plants from the Brunfelsia family, which has convulsant and neurotoxic effects. Symptoms are similar to poisoning from strychnine and can last from a few hours up to several days. Brunfelsamidine is found in Brunfelsia grandiflora , Nierembergia hippomanica and Nierembergia linariifolia. It is a fairly common cause of poisoning among domestic animals such as cows and dogs that eat the plant.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051119 (Brunfelsamidine)


  Mrv1533004161504562D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 N   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 N   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  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
M  END
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3D MOL for NP0051119 (Brunfelsamidine)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -3.0268   -1.3127   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879   -1.2333   -0.5243 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984   -0.2160   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552    0.8195    0.5580 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440   -0.1174   -0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -1.0555   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186   -0.6077   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554    0.5809    0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    0.8866    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8510    1.3933    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015    1.0122    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -1.9852   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348   -1.1119   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847    1.1615    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747    1.7858    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  2  0
  3  5  1  0
  5  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  4 10  1  0
  4 11  1  0
  2  1  1  0
  9 15  1  0
  8 14  1  0
  7 13  1  0
  6 12  1  0
M  END
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3D SDF for NP0051119 (Brunfelsamidine)


  Mrv1533004161504562D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 N   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 N   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  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=N)C1=CNC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H7N3/c6-5(7)4-1-2-8-3-4/h1-3,8H,(H3,6,7)

> <INCHI_KEY>
XVEVWOAHSYZRQE-UHFFFAOYSA-N

> <FORMULA>
C5H7N3

> <MOLECULAR_WEIGHT>
109.132

> <EXACT_MASS>
109.063997237

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.045331994006062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-pyrrole-3-carboximidamide

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.026401596999999923

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.582813679644307

> <JCHEM_PKA_STRONGEST_BASIC>
11.336479035297167

> <JCHEM_POLAR_SURFACE_AREA>
65.66

> <JCHEM_REFRACTIVITY>
42.4893

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brunfelsamidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0051119 (Brunfelsamidine)

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PDB for NP0051119 (Brunfelsamidine)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  N   UNK     0      -0.274   4.390   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.393   4.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+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  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+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 NP0051119 (Brunfelsamidine)
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SMILES for NP0051119 (Brunfelsamidine)
NC(=N)C1=CNC=C1
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INCHI for NP0051119 (Brunfelsamidine)
InChI=1S/C5H7N3/c6-5(7)4-1-2-8-3-4/h1-3,8H,(H3,6,7)
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View in JSmol
SynonymsNot Available
Chemical FormulaC5H7N3
Average Mass109.1320 Da
Monoisotopic Mass109.06400 Da
IUPAC Name1H-pyrrole-3-carboximidamide
Traditional Namebrunfelsamidine
CAS Registry NumberNot Available
SMILES
NC(=N)C1=CNC=C1
InChI Identifier
InChI=1S/C5H7N3/c6-5(7)4-1-2-8-3-4/h1-3,8H,(H3,6,7)
InChI KeyXVEVWOAHSYZRQE-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
Brunfelsia grandifloraPlant
Nierembergia hippomanicaPlant
Nierembergia linariifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as substituted pyrroles. These are heterocyclic compounds containing a pyrrole ring substituted at one or more positions.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrroles  
Sub ClassSubstituted pyrroles  
Direct ParentSubstituted pyrroles  
Alternative Parents
Substituents
  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Carboximidamide
    • 

  • Carboxylic acid amidine
    • 

  • Amidine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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-0.44ALOGPS
logP-0.026ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)16.58ChemAxon
pKa (Strongest Basic)11.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.49 m³·mol⁻¹ChemAxon
Polarizability11.05 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 IDC00002024  
Chemspider IDNot Available
KEGG Compound IDC10133  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBrunfelsamidine  
METLIN IDNot Available
PubChem Compound176662  
PDB IDNot Available
ChEBI ID3195  
Good Scents IDNot Available
References
General ReferencesNot Available