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Showing NP-Card for Nicotine-1'-N-oxide (NP0086802)

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Record Information
Version2.0
Created at2022-05-11 16:31:26 UTC
Updated at2022-05-11 16:31:26 UTC
NP-MRD IDNP0086802
Secondary Accession NumbersNone
Natural Product Identification
Common NameNicotine-1'-N-oxide
DescriptionNicotine-1'-N-oxide, also known as 1'-oxide nicotine, 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. A tertiary amine oxide resulting from the oxidation of the pyrrolidine nitrogen of nicotine. Nicotine-1'-N-oxide is a strong basic compound (based on its pKa). Nicotine-1'-N-oxide can be biosynthesized from nicotine through its interaction with the enzyme dimethylaniline monooxygenase [N-oxide-forming] 3. In humans, nicotine-1'-N-oxide is involved in nicotine metabolism pathway. Outside of the human body, Nicotine-1'-N-oxide has been detected, but not quantified in, several different foods, such as tronchuda cabbages, rapes, cabbages, european cranberries, and chinese chives. This could make nicotine-1'-N-oxide a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086802 (Nicotine-1'-N-oxide)


  Mrv0541 02231219102D          

 13 14  0  0  0  0            999 V2000
   10.9738  -12.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337  -15.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8606  -12.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337  -14.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1156  -12.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -15.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0356  -12.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1626  -14.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -14.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -13.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1626  -15.4329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7807  -12.8855    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.2286  -13.4986    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END
Download

3D MOL for NP0086802 (Nicotine-1'-N-oxide)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -1.5558    0.9968   -1.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9547    0.9102   -0.6038 N   0  0  1  0  0  4  0  0  0  0  0  0
   -0.1599    1.9696   -0.4498 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0189    0.9889    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.4805    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266   -1.1641    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2841   -0.3355   -0.4283 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1138   -0.2626   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -1.0176   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -0.9380   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7662   -0.0924    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.6370    1.4184 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    0.5620    1.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604    1.3877   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -0.0443   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350    1.6490   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    1.6312    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256    1.2920    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -0.6780    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.7070   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751   -2.2244    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133   -1.0778    1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -0.9117   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8268   -1.6763   -1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994   -1.5278   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025   -0.0485    1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604    1.1621    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  7  2  1  0
  9  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  6
 13 27  1  0
 11 26  1  0
 10 25  1  0
  9 24  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D SDF for NP0086802 (Nicotine-1'-N-oxide)


  Mrv0541 02231219102D          

 13 14  0  0  0  0            999 V2000
   10.9738  -12.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337  -15.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8606  -12.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337  -14.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1156  -12.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -15.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0356  -12.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1626  -14.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -14.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481  -13.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1626  -15.4329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7807  -12.8855    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.2286  -13.4986    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END
> <DATABASE_ID>
NP0086802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1([O-])CCCC1C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3

> <INCHI_KEY>
RWFBQHICRCUQJJ-UHFFFAOYSA-N

> <FORMULA>
C10H14N2O

> <MOLECULAR_WEIGHT>
178.231

> <EXACT_MASS>
178.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.186930747586146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate

> <ALOGPS_LOGP>
-1.07

> <JCHEM_LOGP>
0.038159509333333175

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.744453468537048

> <JCHEM_POLAR_SURFACE_AREA>
39.77

> <JCHEM_REFRACTIVITY>
51.6999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicotine 1-N-oxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0086802 (Nicotine-1'-N-oxide)

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PDB for NP0086802 (Nicotine-1'-N-oxide)
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      20.484 -23.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.903 -28.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.006 -22.588   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.903 -27.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.482 -24.053   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.236 -29.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.466 -22.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.570 -27.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.236 -26.498   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.236 -24.958   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      24.570 -28.808   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      21.991 -24.053   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0      20.960 -25.197   0.000  0.00  0.00           O-1
CONECT    1   12                                                            
CONECT    2    4    6                                                       
CONECT    3    7    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8   11    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   12                                                  
CONECT   11    6    8                                                       
CONECT   12    1    7   10   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0086802 (Nicotine-1'-N-oxide)
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SMILES for NP0086802 (Nicotine-1'-N-oxide)
C[N+]1([O-])CCCC1C1=CN=CC=C1
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INCHI for NP0086802 (Nicotine-1'-N-oxide)
InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3
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View in JSmol
Synonyms
ValueSource
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olateChEBI
3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridineChEBI
Nicotine 1-N-oxideChEBI
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acidGenerator
(1's,2's)-Nicotine-n'-oxideHMDB
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridineHMDB
1'-Oxide nicotineHMDB
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxideHMDB
3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridineHMDB
N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridineHMDB
N-Oxide-(1-methyl-2-pyrrolidinyl)pyridineHMDB
Nicotine 1'-oxideHMDB
Nicotine n'-oxideHMDB
Nicotine N(1')-oxideHMDB
Nicotine-1'-oxideHMDB
Nicotine 1-N-oxide, (R)-isomerHMDB
Nicotine 1-N-oxide, dihydrochloride, (S)-isomerHMDB
Nicotine 1-N-oxide, (1S-cis)-isomerHMDB
Nicotine 1-N-oxide, (1S-trans)-isomerHMDB
Nicotine 1-N-oxide, (2S)-isomerHMDB
Nicotine 1-N-oxide, 14C-labeled CPDHMDB
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomerHMDB
Nicotine 1-N-oxide, (1R-cis)-isomerHMDB
Nicotine 1-N-oxide, (1R-trans)-isomerHMDB
Nicotine 1-N-oxide, (S)-isomerHMDB
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomerHMDB
Chemical FormulaC10H14N2O
Average Mass178.2310 Da
Monoisotopic Mass178.11061 Da
IUPAC Name1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate
Traditional Namenicotine 1-N-oxide
CAS Registry NumberNot Available
SMILES
C[N+]1([O-])CCCC1C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3
InChI KeyRWFBQHICRCUQJJ-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
    • 

  • Alkaloid or derivatives
    • 

  • N-alkylpyrrolidine
    • 

  • Trialkyl amine oxide
    • 

  • Heteroaromatic compound
    • 

  • Pyrrolidine
    • 

  • Azacycle
    • 

  • N-oxide
    • 

  • Trisubstituted n-oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic zwitterion
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen 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-1.1ALOGPS
logP0.038ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)4.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.7 m³·mol⁻¹ChemAxon
Polarizability19.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001497  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022656  
KNApSAcK IDNot Available
Chemspider ID396  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound409  
PDB IDNot Available
ChEBI ID30734  
Good Scents IDNot Available
References
General References