ContaminantDB: N'-Nitrosoanabasine (NAB)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-20 16:17:52 UTC

Update Date

2016-11-09 01:15:20 UTC

Accession Number

CHEM016175

Identification

Common Name

<i>N</i>'-Nitrosoanabasine (NAB)

Class

Small Molecule

Description

N'-Nitrosoanabasine (NAB) is a minor tobacco alkaloid that is derived from the tertiary amine known as anabasine (PMID: 3286030). It belongs to a group of nitrosamines called tobacco-specific nitrosamines (TSNAs). It is thought that during tobacco processing, minor alkaloids such as NAB originate from bacterial action or oxidation (PMID: 29751076). Nitrosamines are chemically stable compounds under physiological conditions, but they are known as causative factors for cancers of the lung, pancreas, esophagus, and oral cavity (PMID: 29751076). Activation of TSNAs through α-hydroxylation leads to binding of TSNA to DNA and other cellular macromolecules. This results in biological actions such as carcinogenicity, mutagenicity, embryopathy and other teratogenic actions (PMID: 4997817). N'-nitrosoanabasine is only found in individuals who smoke or who are exposed to tobacco smoke.

Contaminant Sources

IARC Carcinogens Group 3
Tobacco Smoke Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(1-Nitroso-2-piperidinyl)-pyridine	Kegg
N'-nitrosoanabasine, (+-)-isomer	HMDB
N'-nitrosoanabasine, (S)-isomer	HMDB

Chemical Formula

C₁₀H₁₃N₃O

Average Molecular Mass

191.230 g/mol

Monoisotopic Mass

191.106 g/mol

CAS Registry Number

37620-20-5

IUPAC Name

3-(1-nitrosopiperidin-2-yl)pyridine

Traditional Name

3-(1-nitrosopiperidin-2-yl)pyridine

SMILES

O=NN1CCCCC1C1=CN=CC=C1

InChI Identifier

InChI=1S/C10H13N3O/c14-12-13-7-2-1-5-10(13)9-4-3-6-11-8-9/h3-4,6,8,10H,1-2,5,7H2

InChI Key

BXYPVKMROLGXJI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
1-nitrosopiperidine
Piperidine
Pyridine
Heteroaromatic compound
Organic n-nitroso compound
Azacycle
Organoheterocyclic compound
Organic nitroso compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

citraconoyl group (CHEBI:82507 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.08 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.46	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	45.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.32 m³·mol⁻¹	ChemAxon
Polarizability	20.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-1900000000-dd8105864573fc004727	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-013977f2c6fda88acd25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qc-0900000000-9179722f24c850b6c430	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc0-8900000000-0c2cea4a2db968797ec2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-560c30f02c22be3af4b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-1900000000-718e27224fb00b1ad8ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-aa32cd08fe30d1e5d2f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-1900000000-04b6843c996a27751dc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054x-2900000000-98ffe6b8797db154283d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9600000000-357f471b7aa5832862f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-d5f59b970051e63a9dab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1900000000-18eddd1a2e9cdaa3bac9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06uu-9700000000-963b14a1bc1d3f6878f5	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041939

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

13696

ChEBI ID

Not Available

PubChem Compound ID

14335

Kegg Compound ID

C19477

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Hecht SS, Hoffmann D: Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis. 1988 Jun;9(6):875-84. doi: 10.1093/carcin/9.6.875.

2. Konstantinou E, Fotopoulou F, Drosos A, Dimakopoulou N, Zagoriti Z, Niarchos A, Makrynioti D, Kouretas D, Farsalinos K, Lagoumintzis G, Poulas K: Tobacco-specific nitrosamines: A literature review. Food Chem Toxicol. 2018 Aug;118:198-203. doi: 10.1016/j.fct.2018.05.008. Epub 2018 May 8.

3. Magee PN: Toxicity of nitrosamines: their possible human health hazards. Food Cosmet Toxicol. 1971 Apr;9(2):207-18. doi: 10.1016/0015-6264(71)90306-3.

<i>N</i>'-Nitrosoanabasine (NAB) (CHEM016175)

Structure for CHEM016175: <i>N</i>'-Nitrosoanabasine (NAB)