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Showing NP-Card for 2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane (NP0162625)

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Record Information
Version2.0
Created at2022-09-02 21:03:54 UTC
Updated at2022-09-02 21:03:54 UTC
NP-MRD IDNP0162625
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
DescriptionEpibatidine belongs to the class of organic compounds known as epibatidine analogues. Epibatidine analogues are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]Heptane in exo position. Epibatidine is a very strong basic compound (based on its pKa). Epibatidine is a potentially toxic compound. It is a powerful analgesic and works by activating nicotinic acetylcholine receptors. 2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane is found in Epipedobates anthonyi. Epibatidine is a toxin found in certain poisonous frogs (Epipedobates tricolour).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)


  Mrv0541 02241205382D          

 14 16  0  0  0  0            999 V2000
    5.0885   -0.4385    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -0.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950   -0.1221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
M  END
Download

3D MOL for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

     RDKit          3D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.6088    0.6777    0.5357 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    0.4220    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553   -0.4835   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308   -0.7034   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    0.0025   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.2000   -0.7107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8702    1.0776   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    0.9967   -0.1001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8686   -0.1782   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -1.3470    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -0.7140    0.5378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3197    0.5456    1.1031 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6310    0.9206    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334    1.0906    0.8248 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -1.0117   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -1.4284   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.9301   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722    1.0471   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.9768   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5648    1.9279    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -0.0914   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971   -0.3307   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7156   -1.4923    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -2.2237   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093   -1.2903    1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0017    0.2650    1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551    1.4749    1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 13  1  0
 13 14  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 14  2  1  0
 11  6  1  0
 12  8  1  0
  3 15  1  0
  4 16  1  0
 13 27  1  0
  6 17  1  6
  7 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  1
 12 26  1  0
M  END
Download

3D SDF for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)


  Mrv0541 02241205382D          

 14 16  0  0  0  0            999 V2000
    5.0885   -0.4385    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -0.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950   -0.1221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=CC=C(C=N1)C1CC2CCC1N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2

> <INCHI_KEY>
NLPRAJRHRHZCQQ-UHFFFAOYSA-N

> <FORMULA>
C11H13ClN2

> <MOLECULAR_WEIGHT>
208.687

> <EXACT_MASS>
208.076726133

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.0612417407603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.8435768270000001

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.53983127735407

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
57.391600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epibatidine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

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PDB for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.499  -0.819   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       8.027  -1.274   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.686  -2.776   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.215  -3.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.085  -2.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.426  -0.684   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.897  -0.228   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.614  -2.641   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.063  -3.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.700  -3.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.252  -3.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.934  -2.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.129  -1.772   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.831  -0.250   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

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3D PDB for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)
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SMILES for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)
ClC1=CC=C(C=N1)C1CC2CCC1N2
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INCHI for NP0162625 (2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)
InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H13ClN2
Average Mass208.6870 Da
Monoisotopic Mass208.07673 Da
IUPAC Name2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
Traditional Nameepibatidine
CAS Registry NumberNot Available
SMILES
ClC1=CC=C(C=N1)C1CC2CCC1N2
InChI Identifier
InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2
InChI KeyNLPRAJRHRHZCQQ-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
Epipedobates anthonyiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epibatidine analogues. Epibatidine analogues are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]Heptane in exo position.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassEpibatidine analogues  
Sub ClassNot Available
Direct ParentEpibatidine analogues  
Alternative Parents
Substituents
  • Epibatidine-skeleton
    • 

  • Pyrrolidinylpyridine
    • 

  • 2-halopyridine
    • 

  • Aralkylamine
    • 

  • Aryl chloride
    • 

  • Aryl halide
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Pyrrolidine
    • 

  • Azacycle
    • 

  • Secondary aliphatic amine
    • 

  • Secondary amine
    • 

  • Organoheterocyclic compound
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.98ALOGPS
logP1.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)10.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.39 m³·mol⁻¹ChemAxon
Polarizability22.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpibatidine  
METLIN IDNot Available
PubChem Compound1204  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]