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

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Record Information

Version

1.0

Created at

2022-05-11 16:31:26 UTC

Updated at

2022-05-11 16:31:26 UTC

NP-MRD ID

NP0086802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nicotine-1'-N-oxide

Description

Nicotine-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. It was first documented in 1994 (PMID: 8068568). This could make nicotine-1'-N-oxide a potential biomarker for the consumption of these foods (PMID: 16584135) (PMID: 16150123) (PMID: 15962330) (PMID: 9229231).

Structure

MOL 3D MOL SDF PDB SMILES InChI

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

View in JSmol

Synonyms

Value	Source
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate	ChEBI
3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridine	ChEBI
Nicotine 1-N-oxide	ChEBI
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid	Generator
(1's,2's)-Nicotine-n'-oxide	HMDB
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridine	HMDB
1'-Oxide nicotine	HMDB
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide	HMDB
3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine	HMDB
N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridine	HMDB
N-Oxide-(1-methyl-2-pyrrolidinyl)pyridine	HMDB
Nicotine 1'-oxide	HMDB
Nicotine n'-oxide	HMDB
Nicotine N(1')-oxide	HMDB
Nicotine-1'-oxide	HMDB
Nicotine 1-N-oxide, (R)-isomer	HMDB
Nicotine 1-N-oxide, dihydrochloride, (S)-isomer	HMDB
Nicotine 1-N-oxide, (1S-cis)-isomer	HMDB
Nicotine 1-N-oxide, (1S-trans)-isomer	HMDB
Nicotine 1-N-oxide, (2S)-isomer	HMDB
Nicotine 1-N-oxide, 14C-labeled CPD	HMDB
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer	HMDB
Nicotine 1-N-oxide, (1R-cis)-isomer	HMDB
Nicotine 1-N-oxide, (1R-trans)-isomer	HMDB
Nicotine 1-N-oxide, (S)-isomer	HMDB
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer	HMDB

Chemical Formula

C₁₀H₁₄N₂O

Average Mass

178.2310 Da

Monoisotopic Mass

178.11061 Da

IUPAC Name

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

Traditional Name

nicotine 1-N-oxide

CAS Registry Number

Not 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 Key

RWFBQHICRCUQJJ-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

pyrrolidine N-oxide (CHEBI:30734 )
a small molecule (CPD-2743 )

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
logP	-1.1	ALOGPS
logP	0.038	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	4.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.7 m³·mol⁻¹	ChemAxon
Polarizability	19.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001497

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022656

KNApSAcK ID

Not Available

Chemspider ID

396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

409

PDB ID

Not Available

ChEBI ID

30734

Good Scents ID

Not Available

References

General References

Urakawa N, Nagata T, Kudo K, Kimura K, Imamura T: Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. Int J Legal Med. 1994;106(5):232-6. [PubMed:8068568 ]
LeSage MG, Keyler DE, Pentel PR: Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies. AAPS J. 2006 Feb 24;8(1):E65-75. [PubMed:16584135 ]
Court JA, Johnson M, Religa D, Keverne J, Kalaria R, Jaros E, McKeith IG, Perry R, Naslund J, Perry EK: Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking. Neuropathol Appl Neurobiol. 2005 Oct;31(5):522-35. doi: 10.1111/j.1365-2990.2005.00674.x. [PubMed:16150123 ]
Fang Y, Svoboda KK: Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. J Cell Biochem. 2005 Aug 15;95(6):1108-19. doi: 10.1002/jcb.20473. [PubMed:15962330 ]
Eliasson B, Smith U, Lonnroth P: No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis. Eur J Clin Invest. 1997 Jun;27(6):503-9. doi: 10.1046/j.1365-2362.1997.1370689.x. [PubMed:9229231 ]

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

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

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

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

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

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

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

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

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

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

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