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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:01 UTC

Update Date

2023-02-21 17:29:03 UTC

HMDB ID

HMDB0041939

Secondary Accession Numbers

HMDB41939

Metabolite Identification

Common Name

N'-nitrosoanabasine

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3    9                                                       
CONECT    5    1   10                                                       
CONECT    6    3   11                                                       
CONECT    7    2   13                                                       
CONECT    8    9   11                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   13                                                  
CONECT   11    6    8                                                       
CONECT   12   13   14                                                       
CONECT   13    7   10   12                                                  
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0041939
HETATM    1  O1  UNL     1      -0.658  -3.079   0.730  1.00  0.00           O  
HETATM    2  N1  UNL     1      -0.438  -1.901   1.143  1.00  0.00           N  
HETATM    3  N2  UNL     1      -1.038  -0.885   0.390  1.00  0.00           N  
HETATM    4  C1  UNL     1      -2.389  -0.519   0.755  1.00  0.00           C  
HETATM    5  C2  UNL     1      -2.838   0.697  -0.001  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.661   1.672   0.007  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.647   1.122  -0.971  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.272  -0.303  -0.664  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.185  -0.339  -0.387  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.717   0.006   0.838  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.073  -0.028   1.094  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.950  -0.417   0.106  1.00  0.00           C  
HETATM   13  N3  UNL     1       3.431  -0.752  -1.086  1.00  0.00           N  
HETATM   14  C10 UNL     1       2.101  -0.722  -1.346  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.438  -0.261   1.842  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.101  -1.347   0.567  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.731   1.146   0.482  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.019   0.396  -1.045  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.195   1.700   1.009  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.977   2.666  -0.360  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.029   1.176  -2.011  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.230   1.801  -0.932  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.428  -0.950  -1.574  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.998   0.312   1.607  1.00  0.00           H  
HETATM   25  H11 UNL     1       3.416   0.258   2.084  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.015  -0.445   0.302  1.00  0.00           H  
HETATM   27  H13 UNL     1       1.745  -1.007  -2.337  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3
CONECT    3    4    8
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14
CONECT   14   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

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

Chemical Formula

C₁₀H₁₃N₃O

Average Molecular Weight

191.2297

Monoisotopic Molecular Weight

191.105862053

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1133-64-8

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 )

Ontology

Not Available

Exogenous (HMDB: HMDB0041939)

Endogenous

Endogenous (HMDB: HMDB0041939)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.708	31661259
DarkChem	[M-H]-	137.971	31661259
DeepCCS	[M+H]+	142.955	30932474
DeepCCS	[M-H]-	140.234	30932474
DeepCCS	[M-2H]-	176.66	30932474
DeepCCS	[M+Na]+	152.198	30932474
AllCCS	[M+H]+	142.8	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+NH4]+	146.9	32859911
AllCCS	[M+Na]+	148.1	32859911
AllCCS	[M-H]-	145.4	32859911
AllCCS	[M+Na-2H]-	145.7	32859911
AllCCS	[M+HCOO]-	146.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N'-nitrosoanabasine	O=NN1CCCCC1C1=CN=CC=C1	2296.4	Standard polar	33892256
N'-nitrosoanabasine	O=NN1CCCCC1C1=CN=CC=C1	1841.8	Standard non polar	33892256
N'-nitrosoanabasine	O=NN1CCCCC1C1=CN=CC=C1	1838.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosoanabasine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-1900000000-dd8105864573fc004727	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosoanabasine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosoanabasine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Positive-QTOF	splash10-0006-0900000000-013977f2c6fda88acd25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Positive-QTOF	splash10-01qc-0900000000-9179722f24c850b6c430	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Positive-QTOF	splash10-0pc0-8900000000-0c2cea4a2db968797ec2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Negative-QTOF	splash10-0006-0900000000-560c30f02c22be3af4b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Negative-QTOF	splash10-00dl-1900000000-718e27224fb00b1ad8ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Negative-QTOF	splash10-056r-9700000000-aa32cd08fe30d1e5d2f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Negative-QTOF	splash10-006x-1900000000-04b6843c996a27751dc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Negative-QTOF	splash10-054x-2900000000-98ffe6b8797db154283d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Negative-QTOF	splash10-004i-9600000000-357f471b7aa5832862f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Positive-QTOF	splash10-0006-0900000000-d5f59b970051e63a9dab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Positive-QTOF	splash10-0006-1900000000-18eddd1a2e9cdaa3bac9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Positive-QTOF	splash10-06uu-9700000000-963b14a1bc1d3f6878f5	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13696

KEGG Compound ID

C19477

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14335

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:3286030 ]
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. [PubMed:29751076 ]
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. [PubMed:4997817 ]

Showing metabocard for N'-nitrosoanabasine (HMDB0041939)

MOL for HMDB0041939 (N'-nitrosoanabasine)

3D MOL for HMDB0041939 (N'-nitrosoanabasine)

3D SDF for HMDB0041939 (N'-nitrosoanabasine)

3D-SDF for HMDB0041939 (N'-nitrosoanabasine)

PDB for HMDB0041939 (N'-nitrosoanabasine)

3D PDB for HMDB0041939 (N'-nitrosoanabasine)

SMILES for HMDB0041939 (N'-nitrosoanabasine)

INCHI for HMDB0041939 (N'-nitrosoanabasine)

Structure for HMDB0041939 (N'-nitrosoanabasine)

3D Structure for HMDB0041939 (N'-nitrosoanabasine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra