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Showing NP-Card for (+)-Nornicotine (NP0051142)

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Record Information
Version2.0
Created at2022-04-27 22:33:27 UTC
Updated at2022-04-27 22:33:27 UTC
NP-MRD IDNP0051142
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Nornicotine
Description(R)-3-(Pyrrolidin-2-yl)pyridine belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. (+)-Nornicotine is found in Corydalis yanhusuo , Duboisia hopwoodii , Nicotiana acaulis, Nicotiana acuminata, Nicotiana africana, Nicotiana alata, Nicotiana ameghinoi, Nicotiana amplexicaulis, Nicotiana arentsii, Nicotiana attenuata, Nicotiana benavidesii, Nicotiana benthamiana , Nicotiana bigelovii, Nicotiana bonariensis, Nicotiana cavicola , Nicotiana clevelandii, Nicotiana cordifolia, Nicotiana corymbosa, Nicotiana debneyi, Nicotiana excelsior, Nicotiana exigua, Nicotiana forgetiana, Nicotiana fragrans, Nicotiana glauca , Nicotiana glutinosa, Nicotiana goodspeedii, Nicotiana gossei , Nicotiana hesperis, Nicotiana ingulba , Nicotiana kawakamii, Nicotiana knightiana, Nicotiana langsdorffii, Nicotiana linearis, Nicotiana longibracteata, Nicotiana longiflora, Nicotiana maritima, Nicotiana megalosiphon, Nicotiana miersii, Nicotiana nesophila, Nicotiana noctiflora, Nicotiana nudicaulis, Nicotiana occidentalis, Nicotiana otophora, Nicotiana paniculata, Nicotiana pauciflora, Nicotiana petunioides, Nicotiana plumbaginifolia, Nicotiana raimondii, Nicotiana repanda, Nicotiana rosulata, Nicotiana rotundifolia, Nicotiana rustica , Nicotiana setchellii, Nicotiana simulans, Nicotiana solanifolia, Nicotiana spegazzinii, Nicotiana stocktonii, Nicotiana suaveolens, Nicotiana sylvestris, Nicotiana tabacum , Nicotiana thyrosiflora, Nicotiana tomentosa, Nicotiana tomentosiformis, Nicotiana trigonophylla, Nicotiana undulata, Nicotiana velutina and Nicotiana wigandioides. Based on a literature review very few articles have been published on (R)-3-(Pyrrolidin-2-yl)pyridine.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051142 ((+)-Nornicotine)


  Mrv1652304282200332D          

 11 12  0  0  1  0            999 V2000
    2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4186    1.8053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    1.8053    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  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
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0051142 ((+)-Nornicotine)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.7181   -1.4564   -0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732   -0.4615   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474    0.8058   -0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    1.1114   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    0.1434    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308    0.5389    0.1364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2949    0.2059   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953    0.2540   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4510    0.4829    1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.1799    1.2051 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -1.1649    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0858   -2.4766   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7191   -0.6747   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695    2.1577   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465    1.6047    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0894   -0.7855   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    1.0040   -1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294   -0.7060   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257    1.1267   -0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139    0.0537    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496    1.5580    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -1.1857    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -1.9561    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  6  7  1  0
  6  5  1  0
  5 11  2  0
 11  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  7  8  1  0
  4  5  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
  6 15  1  1
  7 16  1  0
  7 17  1  0
 11 23  1  0
  1 12  1  0
  2 13  1  0
  4 14  1  0
M  END
Download

3D SDF for NP0051142 ((+)-Nornicotine)


  Mrv1652304282200332D          

 11 12  0  0  1  0            999 V2000
    2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4186    1.8053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    1.8053    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  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
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CN[C@H](C1)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m1/s1

> <INCHI_KEY>
MYKUKUCHPMASKF-SECBINFHSA-N

> <FORMULA>
C9H12N2

> <MOLECULAR_WEIGHT>
148.209

> <EXACT_MASS>
148.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.690495610322003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2R)-pyrrolidin-2-yl]pyridine

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.7794867553333333

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.921444004927183

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
44.36030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-nornicotine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051142 ((+)-Nornicotine)

Download
PDB for NP0051142 ((+)-Nornicotine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.802   8.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   8.895   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.469   8.125   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.469   6.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.136   5.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.136   4.275   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.381   3.370   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.906   1.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.366   1.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.890   3.370   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0051142 ((+)-Nornicotine)
Download
SMILES for NP0051142 ((+)-Nornicotine)
C1CN[C@H](C1)C1=CC=CN=C1
Download
INCHI for NP0051142 ((+)-Nornicotine)
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12N2
Average Mass148.2090 Da
Monoisotopic Mass148.10005 Da
IUPAC Name3-[(2R)-pyrrolidin-2-yl]pyridine
Traditional Name(+)-nornicotine
CAS Registry NumberNot Available
SMILES
C1CN[C@H](C1)C1=CC=CN=C1
InChI Identifier
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m1/s1
InChI KeyMYKUKUCHPMASKF-SECBINFHSA-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
Corydalis yanhusuoPlant
Duboisia hopwoodiiPlant
Nicotiana acaulisPlant
Nicotiana acuminataPlant
Nicotiana africanaPlant
Nicotiana alataPlant
Nicotiana ameghinoiPlant
Nicotiana amplexicaulisPlant
Nicotiana arentsiiPlant
Nicotiana attenuataPlant
Nicotiana benavidesiiPlant
Nicotiana benthamianaPlant
Nicotiana bigeloviiPlant
Nicotiana bonariensisPlant
Nicotiana cavicolaPlant
Nicotiana clevelandiiPlant
Nicotiana cordifoliaPlant
Nicotiana corymbosaPlant
Nicotiana debneyiPlant
Nicotiana excelsiorPlant
Nicotiana exiguaPlant
Nicotiana forgetianaPlant
Nicotiana fragransPlant
Nicotiana glaucaPlant
Nicotiana glutinosaPlant
Nicotiana goodspeediiPlant
Nicotiana gosseiPlant
Nicotiana hesperisPlant
Nicotiana ingulbaPlant
Nicotiana kawakamiiPlant
Nicotiana knightianaPlant
Nicotiana langsdorffiiPlant
Nicotiana linearisPlant
Nicotiana longibracteataPlant
Nicotiana longifloraPlant
Nicotiana maritimaPlant
Nicotiana megalosiphonPlant
Nicotiana miersiiPlant
Nicotiana nesophilaPlant
Nicotiana noctifloraPlant
Nicotiana nudicaulisPlant
Nicotiana occidentalisPlant
Nicotiana otophoraPlant
Nicotiana paniculataPlant
Nicotiana paucifloraPlant
Nicotiana petunioidesPlant
Nicotiana plumbaginifoliaPlant
Nicotiana raimondiiPlant
Nicotiana repandaPlant
Nicotiana rosulataPlant
Nicotiana rotundifoliaPlant
Nicotiana rusticaPlant
Nicotiana setchelliiPlant
Nicotiana simulansPlant
Nicotiana solanifoliaPlant
Nicotiana spegazziniiPlant
Nicotiana stocktoniiPlant
Nicotiana suaveolensPlant
Nicotiana sylvestrisPlant
Nicotiana tabacumPlant
Nicotiana thyrosifloraPlant
Nicotiana tomentosaPlant
Nicotiana tomentosiformisPlant
Nicotiana trigonophyllaPlant
Nicotiana undulataPlant
Nicotiana velutinaPlant
Nicotiana wigandioidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassPyrrolidinylpyridines  
Direct ParentPyrrolidinylpyridines  
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
    • 

  • Aralkylamine
    • 

  • Heteroaromatic compound
    • 

  • Pyrrolidine
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • 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
logP0.66ALOGPS
logP0.78ChemAxon
logS-0.76ALOGPS
pKa (Strongest Basic)9.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.36 m³·mol⁻¹ChemAxon
Polarizability16.69 ųChemAxon
Number of Rings2ChemAxon
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 IDC00002061  
Chemspider ID83999  
KEGG Compound IDC11360  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93047  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References