NP-MRD: Showing NP-Card for Nicotine 1'-N-oxide (NP0140484)

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Record Information

Version

2.0

Created at

2022-06-29 21:36:42 UTC

Updated at

2022-06-29 21:36:42 UTC

NP-MRD ID

NP0140484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nicotine 1'-N-oxide

Description

(S)-nicotine N(1')-oxide, also known as N-oxynicotine or nicotine-1'-N-oxide, 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. Nicotine 1'-N-oxide was first documented in 2014 (PMID: 25013964). Based on a literature review a small amount of articles have been published on (S)-nicotine N(1')-oxide (PMID: 34906922) (PMID: 24980255).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223362D          

 13 14  0  0  1  0            999 V2000
    0.1624   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -1.7646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.6244    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  2 13  1  0  0  0  0
M  CHG  2   2   1  13  -1
M  END
> <DATABASE_ID>
NP0140484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1([O-])CCC[C@H]1C1=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/t10-,12?/m0/s1

> <INCHI_KEY>
RWFBQHICRCUQJJ-NUHJPDEHSA-N

> <FORMULA>
C10H14N2O

> <MOLECULAR_WEIGHT>
178.235

> <EXACT_MASS>
178.110613079

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.21622599020755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-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>
4.506828011656443

> <JCHEM_POLAR_SURFACE_AREA>
35.95

> <JCHEM_REFRACTIVITY>
51.69990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.303  -1.166   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.521  -3.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.986  -3.294   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.697  -1.233   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.364  -1.166   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    6   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
N-Oxynicotine	ChEBI
Nicotine 1'-N-oxide	ChEBI
Nicotine n'-oxide	ChEBI
Nicotine-1'-N-oxide	ChEBI
Nicotine-n'-oxide	ChEBI
NOX	ChEBI
Oxynicotine	ChEBI
Nicotine 1-N-oxide	MeSH
Nicotine 1-N-oxide, (1R-cis)-isomer	MeSH
Nicotine 1-N-oxide, (1R-trans)-isomer	MeSH
Nicotine 1-N-oxide, (1S-cis)-isomer	MeSH
Nicotine 1-N-oxide, (1S-trans)-isomer	MeSH
Nicotine 1-N-oxide, (2S)-isomer	MeSH
Nicotine 1-N-oxide, (R)-isomer	MeSH
Nicotine 1-N-oxide, (S)-isomer	MeSH
Nicotine 1-N-oxide, 14C-labeled CPD	MeSH
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer	MeSH
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer	MeSH
Nicotine 1-N-oxide, dihydrochloride, (S)-isomer	MeSH
Nicotine-1'-oxide	MeSH

Chemical Formula

C₁₀H₁₄N₂O

Average Mass

178.2350 Da

Monoisotopic Mass

178.11061 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[N+]1([O-])CCC[C@H]1C1=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/t10-,12?/m0/s1

InChI Key

RWFBQHICRCUQJJ-NUHJPDEHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68107

PDB ID

Not Available

ChEBI ID

142659

Good Scents ID

Not Available

References

General References

Poulsen J, Nielsen KA, Bauer-Brandl A: Raman Imaging as a powerful tool to elucidate chemical processes in a matrix: Medicated chewing gums with nicotine. J Pharm Biomed Anal. 2022 Feb 5;209:114519. doi: 10.1016/j.jpba.2021.114519. Epub 2021 Dec 2. [PubMed:34906922 ]
McGuffey JE, Wei B, Bernert JT, Morrow JC, Xia B, Wang L, Blount BC: Validation of a LC-MS/MS method for quantifying urinary nicotine, six nicotine metabolites and the minor tobacco alkaloids--anatabine and anabasine--in smokers' urine. PLoS One. 2014 Jul 11;9(7):e101816. doi: 10.1371/journal.pone.0101816. eCollection 2014. [PubMed:25013964 ]
Craig EL, Zhao B, Cui JZ, Novalen M, Miksys S, Tyndale RF: Nicotine pharmacokinetics in rats is altered as a function of age, impacting the interpretation of animal model data. Drug Metab Dispos. 2014 Sep;42(9):1447-55. doi: 10.1124/dmd.114.058719. Epub 2014 Jun 30. [PubMed:24980255 ]

Showing NP-Card for Nicotine 1'-N-oxide (NP0140484)

MOL for NP0140484 (Nicotine 1'-N-oxide)

3D MOL for NP0140484 (Nicotine 1'-N-oxide)

3D SDF for NP0140484 (Nicotine 1'-N-oxide)

3D-SDF for NP0140484 (Nicotine 1'-N-oxide)

PDB for NP0140484 (Nicotine 1'-N-oxide)

3D PDB for NP0140484 (Nicotine 1'-N-oxide)

SMILES for NP0140484 (Nicotine 1'-N-oxide)

INCHI for NP0140484 (Nicotine 1'-N-oxide)

Structure for NP0140484 (Nicotine 1'-N-oxide)

3D Structure for NP0140484 (Nicotine 1'-N-oxide)