Showing Compound Nicotine-1'-N-oxide (FDB022656)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:31 UTC

Update date

2019-11-26 03:21:05 UTC

Primary ID

FDB022656

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Nicotine-1'-N-oxide

Description

Nicotine N'-oxide (NNO) is a primary metabolite of nicotine, although only about 4-7% of nicotine absorbed by smokers is metabolized via this route. The conversion of nicotine to NNO involves a flavin-containing monooxygenase 3 (FMO3). It appears that NNO is not further metabolized to any significant extent, except by reduction back to nicotine, which may lead to recycling of nicotine in the body. [HMDB]. Nicotine-1'-N-oxide is found in many foods, some of which are thistle, swede, sorghum, and pulses.

CAS Number

63551-14-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(1's,2's)-Nicotine-n'-oxide	HMDB
(1's,2's)-Nicotine-N'-oxide	hmdb
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridine	HMDB
(2S)-N-oxide 3-(1-methyl-2-pyrrolidinyl)-Pyridine	hmdb
1'-Oxide nicotine	HMDB
1'-oxide Nicotine	hmdb
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate	ChEBI
1-methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate	hmdb
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid	Generator
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide	HMDB

Showing 1 to 10 of 36 entries

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
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

Chemical Formula

C10H14N2O

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

178.231

Monoisotopic Molecular Weight

178.11061308

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Nicotine-1'-N-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f96-8900000000-b2b7dd335c3a05aa57bb	Spectrum
Predicted GC-MS	Nicotine-1'-N-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotine-1'-N-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00pi-0900000000-43724ee9d877fcb632a3	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-c5515911fcd12c368c31	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-5900000000-c464534b639004ad3b54	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uec-9300000000-2a2d1afce79d8998d3b3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-4f451a2d6c2540a25c95	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-7b621173e20fa3dd7ce0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-7900000000-1d685bcb46ea923561a3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-403f45bf7fa583376662	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-403f45bf7fa583376662	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-c2850ce6846335b0374d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-d33bcccb60db843c9005	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-c1bca04af770521cb894	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0059-9500000000-d593bd18e59fdd3ed294	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

396

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

409

Pubchem Substance ID

Not Available

ChEBI ID

30734

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01497

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Nicotine-1'-N-oxide (FDB022656)

Structure for FDB022656 (Nicotine-1'-N-oxide)