Np mrd loader

Showing NP-Card for Nornicotine (NP0136925)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-30 16:26:35 UTC
Updated at2022-05-30 16:26:35 UTC
NP-MRD IDNP0136925
Secondary Accession NumbersNone
Natural Product Identification
Common NameNornicotine
DescriptionNornicotine, also known as (+-)-nornicotine or DL-norcitine, 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. There are several routes for the synthesis of nornicotine. → H 2 O A g 2 O {\displaystyle \mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}} } Another route is the partial reduction of 3-myosmine, which can be accomplished by standard catalytic hydrogenation conditions using palladium as a catalyst. Nornicotine is a very strong basic compound (based on its pKa). In humans, nornicotine is involved in nicotine metabolism pathway. One route is the demethylation of nicotine, which can be accomplished by reaction with silver oxide. It is chemically similar to nicotine, but does not contain a methyl group. It is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant. Nornicotine is found in Duboisia hopwoodii, Duboisia myoporoides, Nicotiana africana, Nicotiana alata, Nicotiana excelsior, Nicotiana exigua, Nicotiana glutinosa, Nicotiana paniculata, Nicotiana plumbaginifolia, Nicotiana sylvestris, Nicotiana tabacum, Senegalia berlandieri and Vachellia rigidula. Nornicotine was first documented in 1975 (PMID: 127438). Or with sodium borohydride This reaction gives the racemic product (PMID: 12194923) (PMID: 8245163) (PMID: 15472033) (PMID: 7855117).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136925 (Nornicotine)


  Mrv0541 02231218562D          

 11 12  0  0  0  0            999 V2000
    0.5004    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -0.0483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    0.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.3596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  2  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0136925 (Nornicotine)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.9987    0.8144   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185   -0.3302   -0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491   -1.4244   -0.6358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441   -1.4026   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2750    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -0.3566    0.4678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2039    0.9680    0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646    0.4994    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686   -0.4449   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -1.0524   -0.5616 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606    0.8628    0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    1.7038    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727   -0.3269   -0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624   -2.3214   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -0.9316    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    1.6564   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    1.4226    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8227   -0.1079    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    1.3107    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5809    0.2190   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3798   -1.1843   -0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.0443   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698    1.7454    0.6555 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 NP0136925 (Nornicotine)


  Mrv0541 02231218562D          

 11 12  0  0  0  0            999 V2000
    0.5004    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -0.0483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    0.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.3596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  2  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CNC(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

> <INCHI_KEY>
MYKUKUCHPMASKF-UHFFFAOYSA-N

> <FORMULA>
C9H12N2

> <MOLECULAR_WEIGHT>
148.205

> <EXACT_MASS>
148.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.664988841293663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(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>
10.211523847236988

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
44.3603

> <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 NP0136925 (Nornicotine)

Download
PDB for NP0136925 (Nornicotine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.934   0.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.393  -0.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.095   2.074   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.345  -0.090   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.720   0.547   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.393  -1.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.602   2.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.375   1.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.060  -0.225   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.720  -2.538   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -3.060  -1.765   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3    8                                                       
CONECT    8    4    7                                                       
CONECT    9    5   11                                                       
CONECT   10    6   11                                                       
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0136925 (Nornicotine)
Download
SMILES for NP0136925 (Nornicotine)
C1CNC(C1)C1=CC=CN=C1
Download
INCHI for NP0136925 (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
Download
View in JSmol
Synonyms
ValueSource
(+-)-1'-Demethyl-nicotineHMDB
(+-)-1'-DemethylnicotineHMDB
(+-)-3-(2-Pyrrolidinyl)pyridineHMDB
(+-)-NornicotineHMDB
(R)-3-(Pyrrolidin-2-yl)pyridineHMDB
(R,S)-NornicotineHMDB
(S)-2-(3-Pyridyl)pyrrolidineHMDB
2-(3-Pyridyl)pyrrolidineHMDB
3-(2-Pyrrolidinyl)pyridineHMDB
DL-NorcitineHMDB
L-Nor-nicotineHMDB
NornicotinHMDB
S-(-)-NornicotineHMDB
Nornicotine tartrate, (S)-(R-(r*,r*))-isomerHMDB
Nornicotine, (R)-isomerHMDB
Nornicotine, (S)-isomerHMDB
Chemical FormulaC9H12N2
Average Mass148.2050 Da
Monoisotopic Mass148.10005 Da
IUPAC Name3-(pyrrolidin-2-yl)pyridine
Traditional Name(+-)-nornicotine
CAS Registry NumberNot Available
SMILES
C1CNC(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
InChI KeyMYKUKUCHPMASKF-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
Duboisia hopwoodiiLOTUS Database
Duboisia myoporoidesLOTUS Database
Nicotiana africanaLOTUS Database
Nicotiana alataLOTUS Database
Nicotiana excelsiorLOTUS Database
Nicotiana exiguaLOTUS Database
Nicotiana glutinosaLOTUS Database
Nicotiana paniculataLOTUS Database
Nicotiana plumbaginifoliaLOTUS Database
Nicotiana sylvestrisLOTUS Database
Nicotiana tabacumLOTUS Database
Senegalia berlandieriLOTUS Database
Vachellia rigidulaLOTUS Database
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)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.36 m³·mol⁻¹ChemAxon
Polarizability16.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001126  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022439  
KNApSAcK IDC00042792  
Chemspider ID21108497  
KEGG Compound IDC06524  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNornicotine  
METLIN ID1534  
PubChem Compound412  
PDB IDNot Available
ChEBI ID28313  
Good Scents IDNot Available
References
General References
  1. Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923  ] 
  2. Jacob P 3rd, Yu L, Liang G, Shulgin AT, Benowitz NL: Gas chromatographic-mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. J Chromatogr. 1993 Sep 8;619(1):49-61. [PubMed:8245163  ] 
  3. Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033  ] 
  4. Idris AM, Prokopczyk B, Hoffmann D: Toombak: a major risk factor for cancer of the oral cavity in Sudan. Prev Med. 1994 Nov;23(6):832-9. doi: 10.1006/pmed.1994.1141. [PubMed:7855117  ] 
  5. Schweinsberg F, Sander J, Schweinsberg E, Kollat P: [Examinations of the possibilities to nitrosate nicotine and nornicotine and of the formation of N-nitrosonornicotine in the stomach of smokers (author's transl)]. Z Krebsforsch Klin Onkol Cancer Res Clin Oncol. 1975 Sep 22;84(1):81-7. doi: 10.1007/BF00305692. [PubMed:127438  ]